


Money Shot

by GavinIsaNuisance



Series: Shemales Topping Sissies [1]
Category: Original Work
Genre: 69 (Sex Position), Anal Fingering, Anal Sex, Anal Virgin, Anal creampie, Blowjobs, Butt Plugs, Cock & Ball Torture, Cock Cages, Creampie, Dom/sub, F/M, Face-Fucking, Face-Sitting, Feminization, Forced Feminization, Futanari, Futanari on Male, Humiliation, Money Shot, Orgy, Pegging, Public Humiliation, Rimjobs, Semi-Public Sex, Shemale, Shemale on Male, Spanking, Strap-On, anal penetration, ass, bottom boy, dickgirl, dildo, dominant female, female-male domination, giant cock, humiliated male, sissification, sub boy
Language: English
Status: In-Progress
Published: 2020-06-16
Updated: 2020-07-13
Packaged: 2021-03-03 21:08:02
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 31,485
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24762085
Author URL: https://archiveofourown.org/users/GavinIsaNuisance/pseuds/GavinIsaNuisance
Summary: Shy nerdy virgin Danny is gets a project of a lifetime: photographing his shemale classmate in the nude which leads to new sexual experiences and a new lease on his formerly sex-deprived life. Danny becomes enthralled in the world of being a submissive quickly becoming his new girlfriend's feminized butt boy. He even finally finds a way to romance a classmate of his down the road. Based on a true story.
Relationships: Danny/Tanya
Series: Shemales Topping Sissies [1]
Series URL: https://archiveofourown.org/series/1793206
Comments: 6
Kudos: 81





	1. A Picture's Worth A Thousand Strokes

**Author's Note:**

> All persons depicted in nude/sexual situations are 18 and up. This work is entirely fictitious. Any relationship to actual persons living or dead is unintentional and entirely coincidental.

The University of California Los Angeles. It's commonly referred to as UCLA and is a bastion of pretentious higher learning; not merely because of the criminally low acceptance rate and Ivy League levels of graduate success, but also because of its locale. Most well-respected universities tend to be in or near the worst parts of town, except of course for UCLA. It's located in the upper crust Los Angeles neighborhood of Westwood, a perfect microcosm of upper echelon suburban living, and is literally across the street from the ultra-posh Bel Air neighborhood, you know, where the Fresh Prince lived.

In this place of higher learning was a shy nerdy eighteen year old freshman named Daniel Lowry, who not surprisingly went by Danny. Danny had excellent grades and overflowed with potential so it really disappointed his well-to-do parents that he pursued a major in art and photography, the perfect recipe to a path millennial unemployment and decades of crippling student loan debt, those tuition prices are outlandishly and needlessly expensive.

Danny was not a native to LA, but rather the Bay Area, the combined statistical area encompassing San Francisco, San Jose, Oakland, Concord, and others; including the echo chamber of coastal elitism known as Silicon Valley. Danny was from Daly City, a reasonably sized and very wealthy city just south of San Francisco proper. His father was not surprisingly an important person in the tech industry and his mother a well-to-do environmental activist.

He was a shy boy, boasting with talent, and smile that says: "hello world, I'm a total virgin!"

He had a well-coiffed dirty blonde bowl cut that he often would style up. He had blue eyes, and a very hairless body otherwise. He was very skinny, which often attributed to his shyness, with a flat stomach, spindly arms and legs, with of course an average sized penis. He made up for this in his hips and butt, which was the most bubbly part of his body. He also wore round hipster looking glasses, a perfect finish to his nerdy persona. He was never seen without his Canon 4300 camera always with a variety of lenses, taking very vanilla Norman Rockwell photographs of the picturesque and photogenic Los Angeles landscape.

As his arts major demanded it, Danny was in an experimental photography class taught by Professor Len Hardesy, the perfect embodiment of a Berkeley educated arts professor living in the Silver Lake area, a proverbial slice of Portland, Oregon smack right in the middle of LA. Everyone was at their desks with their latest photography projects as Len was at the white board.

"And as you know, your midterm is a doosy" he explained. "Now for those of you who have heard the rumors about this class, let me put your minds at ease…they're all true" some laughs filled the room. "Much of experimental photography revolves around pushing the envelope so to speak. Some of the most telling pieces of art are the ones our attention is drawn to the most: the ones where we can literally gravitate to the artist's and the subject's vulnerability. Vulnerability is the best indicator to a true and honest piece of art. So, for your midterm, with a partner should you so choose is the most vulnerable art there is: nude art. Now, over the years I have seen everything from the old: photograph covering the crotch, to a secretary pose—which are very common, to a no-shame body positive full frontal expose. Now some, predominantly in middle America refer to this as "pornography" and that's good; because their ignorance to your art is exactly what gets people buzzing. It's what gets you to prove how much you love yourself and your work and how passionate you are. Now, I will be the only one who will view these photos, though some brave souls every year always donate their work to our showcase and as examples for future semesters. Extra credit will be awarded to anyone who chooses this route and I mean major extra credit, like: don't-even-bother-showing-up-for-the-final-extra credit. How does that grab you?" most of the students nodded in agreement.

Danny looked at the bevy of photos that Len was showcasing on the projector screen shining on the white board. Many were in the requisite secretary pose which perfectly hides the more risqué parts of the body. Others were in various poses, some were in fact full frontal with others bending over and showing off their asses, which was making Danny a little weak in the knees. One brazen project was a couple who were dry humping each other.

"I understand this is a major ask for many of you and I am perfectly aware that some of you will not feel comfortable putting yourself out there in such a manor. This is fine, if you do not choose to participate in the project whether you only want me to view and grade your photos or not, you may instead write a seven page term paper, double spaced, five scholarly sources; detailing a nudist author, photo, or movement of your choosing. And yes, you may mesh all three but there must be a defined thesis. Sound good to everyone?" all heads nodded. "Excellent. Those of you who do not have partners, send me an email by the end of the week and if you choose to opt out and write the paper, if so I would like a rough thesis emailed to me by next Friday for my approval. On that note: go shine, everybody" Len finished before dismissing the class.

The shy Danny definitely wanted to do the project, especially if major extra credit was on the line, and any excuse not to do a massive term paper on top of his other research-heavy classes was a good assignment in his book. He definitely wanted to do the assignment with a woman as he wasn't particularly interested of feeling emasculated by another man based on his size. As this was a photography class, the pickings for women were plentiful, Danny was one of four men in the class of fourteen and at least one man was in a relationship with a girl in the class. The other two were quickly snatched up and Danny liked his odds but found that the other women in the class suddenly wanted to do the paper instead.

Danny figured this was because he was a scrawny scrub, but also he was quiet and figured they assumed that the quiet ones were always the dangerous ones. But there was one woman in the class whom nobody dared to ask. Her name was Tanya Cromwell.

Tanya was certainly different from the other twenty-somethings in the class. For one thing she was thirty-five and was one of those who decided to go to school later in adult life once she figured her own problems out. She was a native of South Los Angeles, namely the Chesterfield Square neighborhood. She was African-American, was six feet tall, much taller than the five foot seven inch Danny. She had a cute face, long wavy dark hair and had a very thick body. She had massive DD cup breasts and a huge ass. She always wore skirts and some sort of blouse which always showed off her cleavage. Even women couldn't help but stare. But, what set Tanya apart from the other students was she was openly trans. She made no bones about this, and many of her previous art projects reflected her identity. Though many were afraid to approach her, most likely at the risk of saying something awkward that could be offensive. Danny didn't have such fears and more importantly needed a partner and he knew she needed one too. He knew there would come a point where he would see her naked in all this but was more intrigued than not. Even if was going to be awkward, the record would show that Danny wasn't a prude. He approached Tanya's desk as she was putting her things in her messenger bag, ready for her next class.

"Um, hey, T-Tanya, right?"

"Absolutely. Jerry?"

"Danny."

"My God, I'm so sorry."

"No-no, it's okay. It's easy to mess up and like, I don't talk much."

"That's okay baby, I don't either." Tanya explained.

"So, listen um, I know this sounds awkward, but were you, were gonna do the-the paper?"

"Hell no. I don't wanna take that final."

"Good, um. I don't really have a partner, so…"

"Well sure I'll be yours, Danny. Thanks for having the balls to ask."

"I mean, I didn't really—"

"Everyone else already left. So thank you. Now, I know we have plenty of time, but I am swamped with my other work, is it cool we get this over with like…maybe this week and next?" she asked with a worried face.

"Uh yeah, totally. That sounds good."

"Oh cool, this is working gangbusters already" she playfully punched Danny's arm. "Oh hey, I know we gotta do this shit in the buff…" she then whispered. "You do know I'm trans, right?"

"Yeah-yeah" Danny gulped. "Not a problem. Not, a problem, at all."

"Oh good. I like you already. I figured I'd ask cause I don't want you seeing me full frontal and being all "what! Damn that's big" you know?" she chuckled.

"Yeah" Danny forced a few laughs, but then after realizing he had been laughing for too long grunted and put on a serious face, looking away again. "So like, I'm not from here—I have like a dorm, and like my roommates…it'd be kinda awkward if he, you know, just came in and saw us…"

"Oh fuck yeah. I don't want some limp, strange-ass motherfucker seeing my package, you gotta pay extra for that" she laughed, Danny than chuckled again. "Where you from?"

"Daly City, it's-it's in the Bay, right by San Francisco."

"The Bay's so pretty, I know that for a fact. My dad's from O-town so I know the area" Tanya explained.

"Oh, cool" Danny nodded, trying not to be more awkward.

"Don't you worry, I got the dopest loft in the Arts District. I live alone, and I got two spots for parking. Can you come by today? We can get started?"

"Um, sure. Yeah totally" Danny nodded.

"Great, gimme your number, I'll text you my address."

"Sounds good" Danny nodded. He gave Tanya his number and quickly got a text with her address on it. The two exchanged goodbyes and went their separate ways.

Danny only had one more class that day and his mind was totally on Tanya, especially knowing he'd be seeing her in a compromising position. The two didn't really discuss what they were going to do and the rush of extra credit was starting to wear off and Danny was feeling the awkwardness of what was to come. He wasn't so worried about seeing Tanya, he was actually kind of interested never seeing a trans-woman naked before. He was more afraid of what Tanya was going to think of him, especially seeing his lanky bod and his less-than-impressive dong. But he had little time to think about his insecurities because he found himself driving through the traffic infested Westside of LA and through the syringe-lined roads of Downtown to the Arts District, directly east of the third world marvel that is Skid Row, the largest neighborhood in the United States to be continuously populated by homeless people. It truly was a sight to behold, a literal tent city and rundown storefronts, with the people walking around like zombies, with every conceivable form of trash just scattered everywhere.

Danny finally made it to safety, parking his Nissan Leaf in Tanya's second spot at her loft which was definitely a warehouse or factory at some point in the building's existence like most of the structures in the Arts District. He quickly found himself outside of her loft. He could hear calming music from the inside. He took a deep breath and knocked, though it was the lightest most pussiest knock in the world.

"Be right there!" Tanya called form inside. She must've possessed supersonic hearing.

Danny took another deep breath and forced his head to remain looking straight ahead, knowing full well it would most certainly take a dip low and eye up her mountainous cleavage.

"Hey Tanya, good to see you. Oh, you look nice too. What? Yeah I've been working out, glad you noticed" Danny said barely audible, trying to practice for having something to say to break the awkward.

After a few moments, the door opened, and Tanya stood there, her hair just as wavy but was covering her right eye. She also wore a silk robe. "Hey baby, right on time, come on in, you're letting all the Kush out" she said.

Danny gulped. He had little room to say anything before Tanya ushered him in and closed the door behind them. Terry got a good look around. It was about as artsy a loft as one could get. It had brick walls, with the conventional warehouse ceilings with the exposed vents and fluorescent factory lights overhead. On one wall were a bunch of bay windows with blinds. The place was separated by wall separators and the walls were lined in various photographs taken by Tanya herself. There was a bedroom area to one side with a California King sized bed with silk sheets and a million pillows. Tanya walked to the other side where there was a fully stocked kitchen. In the middle separating all this was a sort of living room area. The only doors were for a closet, and a bathroom near the bedroom area.

The smell of cannabis filled the air and assaulted Danny's nostrils as he watched Tanya over at a breakfast nook area having every bottle of liquor under the sun resting on it, as well as two glasses, and an ice bucket. "Now I know we're both thinking the same thing: this is gonna be awkward as fuck" she explained. Dany nodded feeling good she felt the same way too.

"Totally agree."

"So it would behoove us to clear the mind so we can expose our bodies" Tanya explained poetically. "I feel like crossfading myself, so; you are my guest, what kind of drink can I fix you?"

"Oh um, I'm fine, I'm only eighteen."

"Oh don't gimme that shit, baby. Do I look like a cop to you? What are you drinking? We got vodka—and it's that good Russian shit. Gin, I know this is gonna sound like a stereotype, but we got the Henney, peppermint schnapps but I think one of my girlfriends left that one, Jager, and uh, tequila."

Danny smirked and shrugged, it was free alcohol. "Um, tequila, I guess."

"It's Patrón, that okay?"

"Yeah, thanks."

"Neat, or rocks?"

"Uh, rocks, please" Terry said placing his bag on a nearby couch and took off his shoes, making himself at home.

Terry sat on the couch and eyed up a platter on the coffee table. There was an incents stick slowly burning on top. The platter contained a stone mortar and pestle, some rolling papers, and a pile of cannabis flower next to an ashtray with two roaches already snuffed inside of it, one still partially smoking.

"Here we go" Tanya said, walking over. She handed Danny his glass and sat next to him on the couch, her robe still covering all her sensitive areas. She had herself a glass of Hennessey. Danny took a light sip and winced.

"Me and my girls were gonna get that real mescal shit but my fat ass ain't setting foot in Mexico, know what I'm saying? Those guys down there are thirsty as fuck" she explained.

"Really?" Danny asked.

"Oh yeah. They're so polite, but they don't play down there. They give you one compliment and they think they can just hop in your pants. But I got my secret weapon" she explained, pointing to her crotch which Danny was trying not to notice.

"Huh." He took another sip.

"Yeah, I don't want to sound like a dick but I thought the tourists at least would be a little more looser, but, it's better than some awkward booty sex, you know?" she laughed, finishing her drink. "Oh, where are my manners, please, mi casa es su casa. Want a little hit?" she asked, taking half a joint she was rolling on the table and licked it shut. "It's good stuff, I get it from this dispensary in Van Nuys. Nicest people there, and they have the best product."

Danny took a bigger sip and winced harder. He really needed to settle his nerves but again went for the excuse. "Again, only eighteen."

"You sure?" Tanya asked, handing him the joint she just rolled.

Danny didn't want to be an ungrateful guest. Plus, if there was one thing to open him up in an organic way, it was weed. "You know what, fuck it" he took the joint.

"Atta boy" Tanya produced a plain silver Zippo lighter and flicked it open, and lit it up. She held it under the tip of Danny's joint and he took a nice drag, immediately making the mistake of inhaling too much and coughed.

"Rookie mistake" Tanya smirked. "Gotta inhale light" she said, rolling herself another joint.

"Right" Danny choked. He tried again, taking a lighter puff and immediately felt that euphoric rush of 'it's all good, man'. Tanya finished rolling and quickly joined him, deepening her already noticeable high.

"So, guess we should open with the obvious: ever seen a tranny before?" she asked.

"Nope" Danny choked down another drag. "I thought that was uh, was uh…transphobic term?"

"Oh to some, but I'm not picky. I'm secure with myself. Tranny, shemale, trans, whatever. She/her, by the way."

"He/him" Danny stated his pronouns, finishing his joint, and setting the roach in the ashtray. "Nice place. You were right, it's really dope" he leaned in at the platter of pot. "Can I uh—"

"Oh fuck yeah boy, go for it" Tanya urged him.

"Cool, thank you" Danny nodded before haplessly rolling himself a joint. Tanya stepped in and helped him before all the flower fell onto the floor. "Thanks" he lit up and took smaller puffs this time.

"So, what's your story, Danny? Tell Tanya all I need to know. Cause we about to get a whole lot more personal very soon."

"So I'm like, Danny, uh Lowry. I'm from Daly City, California in San Mateo County—"

"Fuck that shit, come on. Open up. What do you want to do with your life? What are your pleasures?" Tanya asked.

"Uh well, photography. I wanna be a—pro—fessional photographer. Maybe a graphic artist."

"Graphic art is so cool" Tanya agreed. "Lucrative, creative. Whole package."

"Wish my dad would think so. He's a tech guy. Wants me to do the same shit."

"Sounds like my pops. He's a tenured professor over at East Rancho Dominguez. Doctor of African studies if you can find that hard to believe" Tanya chuckled. "Damn, that's good shit."

"He a hard ass too?" Danny asked.

"Mmm-hmm. I went to school a while ago to try the same thing, but realized I wanted to do fashion with some photography on the side. Quit school, did some traveling—some soul searching, came back to LA and here we are."

"What do you do currently?" Danny asked.

"That's what makes this assignment so easy for me. I do nude photographs and I've been dabbling in camera work for porn to make ends meet."

"Oh, cool" Danny gulped, getting awkward again. "You from LA?"

"South-Central, born and raised. Crenshaw High, class of 2004."

"Fuck, man. I was like…a year old when you fucking graduated" Danny chuckled, he then stopped himself after realizing he inadvertently called Tanya old, and quickly deflected. "Galileo Academy in San Fran, class of 2021" Danny explained. "Just graduated last spring."

"How bout the dating game?" Tanya asked.

Danny gulped again, figuring this was payback for the old comment. He took another sip of his now watered down tequila. "Uh, shitty."

"Aw come on, can't be that bad. You're young."

"Nah, I'm a virgin" he sighed, like a virgin.

"No pussy? Any booty?"

"Nope."

"First base, second base?"

"Nada."

"Now be real with me, you just jerk off?" Tanya asked.

"Yeah, totally" Danny said taking another tok and a sip of his tequila.

"But you never tried anything your ass?"

"Nope."

"Not even a little butt plug?"

"I have not."

"Damn boy, nothing?" Tanya asked.

"Yeah. I'm kinda shy."

Tanya slapped his leg. "That shy shit wears off, I promise."

Tanya's movement has slightly opened her robe and off his peripherals, Danny noticed the tip of her dick sticking out. She sat back down in her seat and took another puff from her joint, she then noticed a very high Danny looking at her cock.

"My eyes are up here" she joked.

"Oh-oh, I'm sorry."

"I'm joking, go ahead and stare, I like the attention. Here" Tanya loosened the belt on her robe and seductively removed it. She discarded it off to the side revealing a very thick and nude body with her dick almost at full length.

Danny marveled at its size, especially considering he knew it wasn't fully grown. It certainly was a thick cock though, and fairly long by the length of it. Terry knew it was much larger than his own dick.

"Whoa" was all Danny could muster.

"I take it you're impressed?"

"Uh, yeah, yeah definitely."

Tanya gently started to stroke herself. "Well, come on. We both gotta be nude. Let's go, get it off" she ordered

"O-O-Okay" an apprehensive Danny loosened his belt.

He stood up and dropped his pants revealing a pair of compression shorts where his obvious erection was noticeable. He then removed his shirt revealing his scrawny spindly body, and then finished off with the compression shorts.

"It's not that impressive" he admitted.

"I wouldn't say that. Turn around. Smaller dick usually equals nicer booty."

Danny did as told and bent his ass down a bit over the coffee table, his perfectly hairless ass and ass crack on full display along with his dangling ball sack. Tanya stroked a little harder. "What do you think?" he asked.

"Yeah, that's a butt" she cooed. Danny sat back down, he was now fully erect. "See, you're in the wrong line of work, Danny. That is an ass for fucking."

Danny blushed. "Really, you think so?"

"Hell yes. You need to be greasing that pussy up and spreading those cheeks."

"But, I'm uh, I'm not into dudes" Danny explained dryly.

"I can find you some strap-on chicks that would tap that ass, plus there's gals like me" Tanya winked. "You haven't lived until there's a shot of tranny cum being blasted inside your rectum, believe me. Plus, nothing humbles a man more quite like taking it up the butt."

There was an awkward moment with the two before Tanya finally stood up. "Okay, before this kush puts us to sleep; let's get to work."

"Yeah, good idea" Danny agreed.

The two made their way over to the bed where Tanya already had some directional and flood lights set up for their nude photoshoot. "Okay, this is just a practice run cause I don't know about you, but I want this to be perfect. I'm not taking a final if I can avoid it, know what I'm saying?"

"I totally agree" Danny nodded.

"Okay, then get that camera ready, I just wanna do a few poses like this" Tanya made some cute sexual poses standing up, many with her dick sort of in the shot or she tucked it under her legs. "Okay, now let's go full frontal" She let her dick flop free as Danny made a few more shots. Then Tanya laid on the bed on her back with her legs spread, again, more shots. "Alright, get a little closer, get some boobs in there."

"Okay."

Danny got a bit closer to get some action with Tanya's breasts. He got back and got a few of Tanya stroking her peen as well. "How's this?"

"Perfect. Okay, time to show off my money maker."

Tanya shifted herself around on the bed to on her stomach. She then got up in all fours with her ass completely sticking out. Danny tried to get some shots but was admittedly distracted by the sight of Tanya's massive ass. Hers was also hairless like Danny and his dick was completely hard when he saw her sphincter pucker.

"Now a few more like this."

Tanya got lower, putting her face onto the bed, namely onto one of the many pillows and stuck her ass in the air. Danny got plenty of usable shots, or some usable and some just good jerk-off material.

"How's that?"

"That's perfect. Okay, now it's your turn."

"Okay."

Tanya got up and went to get her camera with a wide array of lenses while Danny put his camera aside and sat on the bed, his dick were clearly sticking up. She got a couple of pics but was not at all satisfied.

"Oh come on, you can do better than that."

"What should I do?" Danny asked.

"It's your midterm."

"I dunno, I don't exactly have a really fit bod for this kind of thing" Danny shrugged.

"Well, you do have something. Let's get some pics of that tush. Come on, nothing says confidence by shoving your naked ass in the air for a photoshoot."

Danny shifted in the bed and got on all fours. "Like this?"

"Yes! Perfect Danny, work it."

Tanya continued to get every angle she could of Danny's dude booty. Danny tried to do the same moves that Tanya was doing while trying to remain secure about the fact he was presenting his ass essentially to this trans-woman with a rock hard dick taking pictures of him. Tanya inched her way closer.

"Alright, now while your ass is up, take your hands and spread your cheeks with them. Spread them as wide as they can go."

"Can do" Danny said muffled into the pillow he was shoving his face into.

Danny reached his hands back and each grabbed a respective pale cheek and pulled them apart, spreading his sphincter with him, which certainly puckered.

"Yeah, that's an ass that's open for business."

Tanya got as many pics as she thought she needed, occasionally using one hand for the photos while using a free hand to stroke herself. She then ended up tripping a bit and quickly recovered, but when she did was right at the edge of the bed and her tip grazed Danny's cheeks.

"Oh my gosh. I'm so sorry."

"No it's okay. Can I take a break?" Danny asked.

"Yeah of course."

Danny let go of his ass and flopped on the bed. He wanted to take a break because the copious amount of weed in his system was breaking down and he was starting to nod off. His high was at its peak and all he wanted to do was sleep.

Tanya had put her camera down and started to feel sweaty from all the hot camera taking…but mostly from the hot studio lights just feet from her. She sat on the edge of the bed. She could hear snoring and knew it had to be Danny. She tried to wake him up.

"Danny…Dan…Danny, wake up" she continued to shake the boy, but it was no use. She sighed and laid on her back. She saw Danny was sleeping on the pillow, hugging it. "I've definitely been in stranger situations" she muttered.

She saw the sleeping eighteen year old. There was something cute the way Danny slept on her bed…even though they barely knew each other and had only been formally introduced mere hours ago. And now they were lying naked in the same bed together. Which was funny how college works, it certainly broadens ones horizons.

Tanya pouted. She was still very horny. She looked over on her nightstand where she had a pre-rolled joint she neglected to smoke sitting in an ashtray. She smiled and took it, as well as the nearby crappy gas station Bic lighter sitting next to it. She sparked up and tossed the piece of shit lighter aside. She got halfway through the joint and laid down on her bed, now in an even greater stage of euphoria than before.

She finished her joint and shoved the roach in the ashtray. She played with her boobs and watched her dick spike up from previously being flaccid from not being inches from Danny's ass. Seeing he was still asleep, Tanya took the opportunity and started to jerk herself off.

This quickly turned into a more furious jerking motion as she vigorously stroked her thick member wishing she could spank this load onto Danny's face. She started to shake the bed. This shaking certainly aroused some sixth sense inside of Danny. This was probably that sense all Californian's have when we feel shaking which is usually followed by the impending ambiguous mercy of an earthquake. Danny rubbed his eyes and looked up, seeing Tanya's long cock being furiously stroked. Tanya looked down and blushed a little seeing Danny watch her jerk off…especially considering she was thinking of him.

"Oh…shit" she chuckled with that high laugh, where literally everything feels funny even when it isn't.

"What are you doing?" a woozy Danny asked.

"Sorry, I didn't…I—" she chuckled. "I didn't know if this was going anywhere. I'm sorry, I had to just—release, you know?"

"Um, sure."

Danny didn't say no and Tanya was too horny not to take his ambiguous silence for anything other than 'it was okay to jerk off'. She continued while Danny inched his way closer to her with his head and shoulders right next to her massive dong. He put a hand on her thigh. A shiver was sent up Tanya's spine as she watched Danny rub her leg. He looked up at her for approval and a bloodshot-eyed Tanya gave him a single nod, all the approval he needed to continue.

Danny moved a hand closer to Tanya's cock. The thick trans-woman moved her hand away while Danny lightly gripped the thick member, his tiny fingers barely able to connect all the way around. Tanya gave him another single nod then put her head back and used both her now free hands to play with her tits. Danny continued to stroke Tanya. It was smooth motions at first Danny very familiar with the art of jerking off, though this would be his first hand-job given to someone else…and it certainly wouldn't be the last.

He laid the side of his cheek on Tanya's leg while he stroked her dick which grew with each pump. Though he was up close and personal with her cock, Danny marveled as to how much it grew in size. He was very stunned just how tall and thick it was.

"Whoa."

"Yeah, I'm a grower, not s show-er" Tanya chuckled.

Danny continued to stroke Tanya's ever growing cock and in is high stupor, he seemed to inch his mouth closer and closer to the side of her shaft, barely even realizing what he was doing. Danny aggressively stroked her dick, sticking his tongue out, it finally touched skin, and he licked up Tanya's shaft like an ice cream cone.

He immediately recoiled after he realized what he was doing. "Oh my God, I am so…s-s-sooo sorry" he murmured. Tanya chuckled.

"Now who told you to be sorry? Or to stop?" Tanya asked with a raised eyebrow. "Keep licking" she ordered.

Danny was now a bit hesitant, especially after Tanya's nonchalantly stern tone. He moved his head away for a moment but then stopped. He relished in this strange opportunity of being told what to do and his dick definitely responded. His pecker got a quick boost after Tanya's demand, and so Danny moved closer. He started again to lick Tanya's cock up and down.

"Ooh, that's it. Yeah, I like that" Tanya moaned.

Eventually, Danny moved up to the top of Tanya's tip, and had a grip on the base of her dick. He gave Tanya a nod as it was obvious what he was about to do next and she smiled, nodding back. Danny moved his face towards the tip and lowered his lips onto it, leaving a trail of saliva dripping down her shaft.

He put his face onto Tanya's member and slowly put an inch or two into his mouth, her tip completely disappearing inside of Danny's face. Danny looked up at Tanya as he slowly licked her cock.

"That's a good girl" Tanya cooed, playing with her breasts. "Come on, get it deeper."

Danny nodded and slowly took a few more inches of her dick inside of his mouth hole. He was leaving saliva falling down Tanya's shaft as he sucked her off. He tried to get a few more inches inside, but realized his gag reflex was kicking in, he got off of Tanya's dick and coughed.

"It's okay, cough it up, you'll get used to it, just take it a few inches at a time" She explained.  
"Will do" Danny wheezed.

He put his mouth back on her dick and slowly put a few more inches inside of his mouth as his spit slipped down into her crotch. He looked up at Tanya who made a jerk-off motion with her hands.

"Aren't you forgetting something?" she asked.

Danny nodded and started to pump her dick harder and harder with his hands. He would look down but would on occasion look back up at Tanya giving her cute puppy eyes while he sucked her off. Tanya enjoyed this very much, watching her eighteen year old classmate chug her massive dick.

Danny was getting the hang of taking Tanya's schlong and was almost to the point where he could completely deepthroat her, as all of her length was now inside of his mouth, and his lips touching her crotch. Tanya swooned.

"Hmm, you should play with my balls a little bit" she casually ordered.

Danny nodded and used his fingers to play with Tanya's sack while he sucked her off. Tanya was overjoyed with Danny's skills, considering this was supposedly the first sexual experience he's ever had. She was skeptical but wondered maybe he was just naturally cut out for this sort of submissive fetish.

"You sure this is your first time?" she asked. "Cause you're a natural at sucking dick" she chuckled.

Danny got off Tanya's dick and smiled, aggressively stroking her. "Why thank you."

He then got right back to work, slobbering on her member while being able to deepthroat it. Tanya turned to her nightstand where she saw another one of her little point-and-shoot cameras sitting there. She used a hand to grab it and aimed it right at Danny's face. "Smile, Danny" she said.

Danny looked up at her surprised, cock still in his mouth and eyes wide as Tanya got a perfect money shot. She got a few more candid pictures as Danny slammed his mouth down hard on her cock. Tanya rubbed the boy's head while he did this and made very audible gulping noises, occasionally stopping to catch a breath, but still wasted no time in stroking Tanya off while he did so.

But a horny Tanya wanted to see more, much more. She rubbed Danny's head and then gently pulled him off of her cock. "What's wrong?" he asked.

"Nothing, but I wanna see some booty, you can get back to work, but stick that rear in my face."

Danny gulped and got up. He then moved his spindly body and straddled Tanya's thicker bod. He bent down so his ass was completely spread and right in front of Tanya's face and got right back to work, sucking her dick.

Tanya smile as she slapped, poked, and prodded at Danny's cheeks. "Yeah, that's what I'm talking about!" she cooed. "This ass was made for fucking."

Tanya spread Danny's cheeks some more before staring right into his hairless puckered sphincter. Tanya licked her right index finger before moving her lubed digit over to Danny's hole, slowly pushing at his entrance until she was able to get the tip inside. She took it out after feeling some internal resistance from Danny and slobbered all over it before sticking it back in.

After some puckering, Tanya's finger got past his anus and deeper inside of his rectum. She felt satisfied as she fingered the boy, and feeling Danny not wincing at the thought of being penetrated for the first time.

But Danny was so high at that point that he barely noticed, and was in a euphoric state of ecstasy from sucking off Tanya's massive dong. But Tanya wasn't satisfied, she used her index finger to stretch out his anus to accommodate her middle finger, and effectively stretched his asshole out.

Danny now started to notice the anal invades inside of him and made soft moans, which did not go unnoticed by Tanya. "Yeah, that's right, I'm in your ass now" she chuckled.

Tanya saw that Danny was really liking this because she saw his dick was rock hard. With quick thinking, Tanya made a move and reached with her mouth for his ball sack and gently bit down on it.

After Danny moaned from some ball torture, Tanya let go and used her free hand to move his dick down towards her awaiting mouth, and the two were now in a 69. Danny let out a loud and muffled moan after realizing his dick was now inside of Tanya's mouth.

Tanya moved her head onto the bed and off while deepthroating Danny, which his smaller dick was easy to fit inside of her throat. She could tell he was close from all this newfound sexual stimulation, especially from getting pleasure from having his ass fingered.

She stuck her fingers in deep before shoving his cock deep inside of her own mouth. Danny almost had to stop himself from sucking on Tanya or else he might have bitten down hard on her cock. He vigorously pumped her dick while getting his mouth deep onto her member, now both of them were veiny and close.

Danny could feel his tiny dick throb. Tanya could to. She knelt her head up to get every last inch of his cock before using her free hand to slap his balls, which was all the stimulation he needed to cum. Danny grunted as thick waves of cum flowed into Tanya's mouth thanks to gravity and the thick trans-woman drank it all up.

Danny moaned as he could feel Tanya ready to fire. She was stimulated from the blowjob and with one final suck Danny was all the way down, perfect for when Tanya shot hot loads of cum right into Danny's throat. Danny drank up, but it was so much cum, he almost threw it back up. He got his mouth off of Tanya's dick and let the rest of the cum shoot onto his face and Tanya's crotch.

Eventually this subsided and Tanya got her fingers out of Danny's butt. The two collapsed next to each other. Tanya got a good look At Danny's cum covered face and the boy smiled. "Did we just do that?" Danny slurred.

"Hell yeah."

"So, what now?"

"We sleep. No way your stoned drunk ass is going home."

"Are you sure?"

"Boy just shut up and get your cute ass over here" Tanya smiled.

She curled up next to Danny and the two laid in bed. Tanya turned off the light and reached under the bed to tear off the extension cord to the studio lights. It hadn't hit the other as to how that happened, but it did. Danny was the first to drift off to sleep, cum still on his face. Tanya took some time, wondering what all this meant, but knowing she liked Danny, and wondered exactly what the future would bring. She hoped for good news, but the two were definitely very drunk and very high, it would be a different conversation when they were sober the next day.

But that was a conversation for another day. Tanya then reminisced about their sexy romp before shutting her eyes and falling asleep herself.


	2. Uh, I Can Explain

**Summary for the Chapter:**

> Feeling restless, Danny wakes up to go to Tanya's bathroom and his curiosity turns to a wall mounted dildo in her shower. The situation goes from good to great when Tanya catches him in the act and a very sensual shower ensues.

Danny and Tanya slept with their bodies intertwined and cuddled with one another. Some time had passed, and their high and drunk had worn off. As comfortable as they were this wouldn't last, particularly for Danny.

Not soon before long, he woke up, instantly realizing he wasn't in his uncomfortable single bed in his uncomfortably small dormitory, but was in this spacious California King sized bed in a swanky loft in the not-so-swanky Arts District of Downtown LA.

But that wasn't just what hit Danny, what hit him right in the face…well, was Tanya's dick, because he had sucked her off to the point where she came all over his face, a completely new experience for the eighteen year old, considering he went on a stoned diatribe about his own virginity. He didn't quite know how he felt sucking off his trans class partner, or from having his trans class partner finger his asshole while he sucked her off and with Tanya openly wishing to fuck his booty hole with her cock.

One thing he thoroughly enjoyed was the 69, where Tanya sucked him off and drank his juices, almost as simultaneous as her orgasming on his face. But, what was for certain, was that Danny didn't want to be around when Tanya woke up, because he was a bit embarrassed on the subject, and figured their run-ins couldn't always feature booze and weed to help placate the awkward.

Plus, he couldn't avoid Tanya forever, they not only had class but were working on this project together. The problem was Danny just didn't know how to feel, he really wanted to be the one on top and fuck some hot chick's pussy like everyone else, and there was something to the potential pain of being rammed by Tanya's massive dick that seemed foreboding. Danny could already feel his partially virgin ass quiver with the thought.

But, his thoughts were sidetracked by the feeling of needing to pee, as copious amounts of alcohol will do that to you. Danny sneaked out of Tanya's bed and fumbled around the dark apartment searching for her bathroom which was clear on the other side of the loft.

He tip toed into the bathroom, and turned on the lights, and was again taken aback by how spacious it was, considering the loft was merely just that, a loft. It had your usual bathroom fare, a toilet, sink with a vanity mirror and tons of makeup on the sink counter, and a jacuzzi tub with a shower head.

Danny quickly relieved himself in Tanya's toilet, which was a much longer pee than he anticipated. While he did this, something caught Danny's eye. He turned to see something mounted on the wall of the shower, a foot or so above the tub.

It was a wall mounted dildo. It looked like your average run-of-the-mill suction cup dick, it was colored in a creamy skin color, made of silicon, but bad a golden bulge at the end between the shaft and the suction cup. Attached to that was a hose and a squeezable grip, the kind you see on a blood pressure gauge.

Danny was extremely curious. He washed his hands, not being able to take his eyes off of the cock. He was about to leave and try to go back to sleep, or better yet, try to get dressed and get the fuck out of there, but yet he couldn't. He was too mesmerized by this suction cupped dildo to the wall. He felt like he had to take a closer look, after all, he never saw one before in real life.

He inspected the dangling dildo, it was a generic silicon cock. He even smelled it, and it smelled like plastic. He started to fondle it a bit. His fondling started out small, the way he had stroked Tanya, but then moved to more aggressive petting. His own cock started to rise and he stroked it with his free hand.

Not thinking about consequences, he soon realized what he wanted: to suck this fake dick. Tanya wasn't around and he felt, maybe he can use this as an experience to prove he was pretty good at chugging a dong. Or perhaps he was just too horny and had too many thoughts floating about his head to think clearly? While it's probably the second one, Danny nevertheless knelt on the tub's floor in front of the dick, still stroking it.

Much like before, Danny licked the outside of the tip while using a hand to stroke the cock while the other hand stroked himself. Danny's licks were more aggressive and he used a little teeth considering biting this dick wouldn't have unintended consequences.

While licking the tip, he realized the hole of the dick was hollow, which he felt off but figured it was just for accuracy, right? Danny spit all over the tip and shoved it into his mouth, creating entrails of saliva dripping from the shaft as he licked it.

Danny slurped the dick down, constantly stroking it, getting it slicked up in his spit. His gag reflex was improving from sucking Tanya off before. True, this dick wasn't as long or as girthy as Tanya's, but it wasn't a beginner's dick either. Danny was pretty impressed with himself after only one day of eating cock.

He stopped stroking and put his hands against the wall trying to get the dick as deep into his throat as he could. The first was sort of a fail and he coughed, taking his mouth off the dick and leaving a wet saliva trail in his wake. I guess he didn't know his own strength? He tried again, getting much deeper and getting the tip just into the opening of his esophagus.

The next attempt, after he vigorously stroked the fake dick shoved his entire mouth on it and this this time it got to as deep as the bulging sack nestled between the shaft and suction cups. Danny stopped, his dick dripping with pre-cum. Now, he wanted more…

He was too horny to just give up and he used his mouth to defile Tanya's toy anyhow. He was admittedly curious about sticking a foreign object up his anus, especially considering Tanya put the thought into his stoned head a mere few hours beforehand. Once again his horny mind figured maybe he could learn how to take a dick in his ass. It was obvious Tanya wanted to but Danny wasn't ready to have that monster dong pound him in the butt.

His mind made up, he grabbed a bottle of shampoo, and lathered up the cock before spreading some down his crack and sticking a few lubed fingers inside his hole to both stretch it out and slick up his rectum.

Satisfied, he then bent himself over, making sure his hands were touching the tub. He moved his asshole right onto the tip and tried to force into his ass, both the tip and his hole were so lubed up it merely slipped away. He used one hand to help move the dick into place and tried to push it in. Danny grunted as the resistance from the big dick couldn't get passed his sphincter and he stopped.

Taking a deep breath, Danny tried again, and this time he got the tip past his opening, but the pain quickly became too much and he failed again, his asshole puckering. On the third attempt, however, Danny finally forced it through and after the first few seconds of pain subsided, the dick slicked it's way up Danny's rectum, and he had to bite down on his lower lip in order not to moan.

Wow, that's what this felt like? It was a painful few seconds, but after that was over, it was kind of hot. Danny blushed as he worked his body back and forth on the wall mounted cock as slowly as he could, and his dick instantly became hard as a rock, like it wasn't already.

Danny stood up a bit more but was still bent down. He continued to move is hips and lower back, thrusting them on the cock as his asshole was stretching itself out wide enough to comfortably accommodate the cock, and Danny finally started to respond positively from the self-imposed ass pounding.

Little did he know, he was about to have an admirer…

Danny wasn't exactly quiet in his effort to make it to the bathroom, and his constant coughing and gagging on the wall mounted cock now shoved up his ass alerted the sleeping Tanya. She too had awoken, and at first assumed Danny had merely left her, which made her disappointed, but upon further inspection and seeing the bathroom light on from across the loft she figured there was either an intruder who desperately had to pee, or it was Danny. Obviously the first was true.

She tiptoed towards the bathroom, seeing first that the door was cracked just in the right spot for her to catch a glimpse of her eighteen year old horny house guest pounding his own ass with HER dildo. Tanya did think to herself she never did tell Danny about her dildo, it was very much out in the open and maybe a warning could have been nice as this wasn't just something you found in a person's shower.

Though she never told him about it, that didn't give him license to simply fuck himself on it! But, as much as Tanya wanted to barge in and confront Danny, which would certainly be at the most inopportune of moments to do so she merely waited outside the door, just far enough removed from the light so Danny wouldn't see her if he so chose to look.

Tanya watched Danny fuck his own ass on the fake cock while noticing hers was starting to tent pole from this voyeuristic adventure. She stretched her flaccid cock out, never taking her eyes off the boy shoving his ass onto her wall mounted dick.

Inside the bathroom, Danny picked up a good rhythm as his rectum was now completely stretched from having the cock wedged inside his hole. His dick was also dripping in pre cum from furiously jerking it while the dick massaged his prostate. He was ready to cum soon.

He was getting to the point where he would shove several inches in at a time then push off and then back in harder. He did this for several attempts until his cheeks met with the bulging balloon near the base of the dick. He grunted as he moved his hips and tried not to moan from the dick pounding his butt, though he wanted to.

Danny secretly wished this was Tanya fucking his ass. Though he didn't want to disappoint Tanya with constant moaning and whining from the growing pains of losing his anal virginity. He figured he'd rather be more seasoned should he ask her to fuck him, knowing her monster cock would certainly tear him up.

Outside, Tanya's cock was fully grown as she watched Danny literally fuck himself. She was hoping she would barge in and Danny would beg her to fuck him in the ass but if that were the case she wasn't going to deliver. Mostly as punishment for just servicing his tushy on her dildo without her knowledge, but also she wanted to dictate the fucking on her terms.

There was something cute to her about Danny's shy nature and she wanted to use that to her advantage. But, in the meantime she still wanted to enjoy her time with him. With her dick perfectly hard, she walked off to briefly grab her camera and headed over to the bathroom.

Inside, Danny was ready to fire his load onto the floor of Tanya's jacuzzi tub. He shoved the dick as deep as it would go and grunted as it filled him up with its girth. But of course just before Danny could finish off, the door flung open and Danny stood wide eyed as Tanya stood there, looking right at him with a raised eyebrow.

"Uh…I can explain" Danny said dryly, a thin line of blush eclipsed his face.

"Alright, start explaining. While you do, you mind sticking your booty out just a 'lil bit, Danny?"

"Oh come on" Danny complained.

"Call it a punishment for using my dildo without asking me. Now stick that ass out" she ordered.

Danny sighed and did as he was told. "Good boy, now pout for me, pout from fucking yourself on my fake cock" Tanya ordered as she took some more snap shots.

"Like this?" Danny asked, actually pouting and not acting as he was sort of annoyed that he was being used for photos Tanya would most likely jerk herself off to at some point.

"Yeah, just like that" Tanya smiled. "Alright, jerk that tiny cock of yours while you fuck your own ass."

"Okay"

Danny grunted as he furiously masturbated while Tanya humiliated him further by taking more photos. Danny felt it easier to jerk off now, there was something sexual about being ordered by Tanya while she snapped candid photos of his self-imposed anal ramming. His dick was leaking juices but he shoved the last bit of the cock inside of him which was enough to put him over the edge as his dick shot out a few loads of jizz, landing on various places on the tub floor. Finally, they were merely drips.

Tanya smiled, satisfied as she got many photos of Danny for her own sexual amusement. Danny sighed and winced as he let the cock fall out of his ass, which it did with a pop, and dripped in the makeshift lubricant Danny used to grease it up. His asshole also dripped in the shampoo lube, and gaped.

"See, that wasn't so bad now was it?" Tanya asked.

"Nope, it was kind of hot" Danny grunted almost falling over as the pain of the cock falling out became real.

"I figured you'd like that. I told you, your ass was made to be fucked."

"I'm starting to agree with you. But uh, I'm not sure I'm ready for you yet" Danny explained.

"Now, who says I'm just gonna pound your little white booty cause you asked?" Tanya raised an eyebrow. "Nah, we're doing this on my terms, boy" she insisted. "Maybe I'm not ready for some virgin boy pussy just yet. Besides, it's more fun to keep you guessing."

"Is that what hard to get is?" Danny asked.

"In a way. If you wanna fuck yourself on your terms, then I'll fuck you on mine. Now come on, we're still covered in dried cum and drool, we're already in the shower, we should clean ourselves up…unless you got other chick's dildos you wanna sit on?"

"No-no, I'm good."

"Then move over."

Tanya hopped into the shower and closed the curtain. She had good water pressure on her waterfall shower head, and the two took turns standing under it and letting the warm water wash over their bodies.

It slowly built up to a suitable temperature for the two of them. While Danny moved around and let the water cascade over him, Tanya groped his girly ass on occasion and stretched his cheeks out.

"I can't believe you just went and pounded your cute little ass." Tanya chuckled.

"I'm sorry."

"No-no, I'm joking, it was hot, really" Tanya admitted. "And while I do want to wait before we fuck I gotta say, I am definitely interested. You got a hot little butt" she said spanking and stretching his cheeks.

"Why thank you."

Tanya got out some body wash and lathered herself up. She squirted some onto Danny and washed his body. The two took turns seductively washing one another, Danny blushing while he got to Tanya's mid-section. He was right below her very large breasts and winced.

"It's alright, you can touch. We got far more personal than this already." She explained.

Danny nodded and started to immediately play with Tanya's boobs. It started out merely washing them, but then it morphed into squeezing them and fondling her tits as well. Soon, it wasn't just for washing purposes, but for no other reason than to grope her.

Tanya liked the attention her boobs were getting. She decided though that she wanted more, given Danny's lack of boundaries; and shoved his head into her breasts. Danny licked around her boobs and found his way to her right tit.

"That's good. Lick momma's breasts" she cooed.

Danny suckled on her tit, and used his free hand to massage her other boob. He would occasionally bite down which made Tanya wince and coo in pleasure, which not to mention made her dick hard.

Danny would switch back and forth from breast to breast, while sometimes motor boating the middle of her bosom, because his inexperience in sex taught him that women like that sort of thing. But Tanya did get a chuckle out of it.

While he did this, Tanya reached down and groped his dick and balls, letting the soap wash off of them. She could feel Danny's little cock getting hard again slowly from all the attention. Tanya felt her nipples getting hard from Danny's biting on them. She wanted more, and figured she knew just how she would get it. From behind her, she rubbed the wall mounted dick and it was still very soapy from Danny fucking himself on it.

"Ooh, baby" Tanya moaned. "You wanna watch how I fuck myself?" Tanya asked.

Danny released from her tits. "Oh yeah."

"Good." Tanya cooed and reached behind her to use her fingers to stretch her asshole out. She motioned to Danny "Take the shampoo and lube that shit up again" she ordered.

Danny did as he was told and spread some shampoo on the cock while he watched Tanya finger her own ass. After she was satisfied, Danny moved out of the way and Tanya removed her fingers and spread her massive booty over the cock, slowly pushing herself in. Danny watched as she was inching the dick past her sphincter one millimeter at a time.

"You see…" she grunted. "You can't just…you can't just shove all that in, that's a nine inch dick, it's gonna…fly right out unless…you inch it in, you know?"

"I can see that" Danny nodded.

"You gotta train your ass slowly, there's no need to rush anal…ooh yeah, sex" Tanya continued.

She got the full tip inside of her and moved back and forth with just the couple of inches before sliding the rest in after her hole gave in and the dick invaded Tanya's ass. She began to move her hips on the thing, in faster and more uniform rhythm than the inexperienced Danny.

"See, this is how you do it" she said.

Danny nodded as he watched Tanya's booty bounce on the cock. It wasn't long before Tanya got a fully rhythm and pushed her entire body on and off the dick like a seasoned pro, practically being able to shove the golden bulge into her asshole.

The boy looked down and saw Tanya's cock was fully grown. His gaze turned into slowly stroking her dick with his hands. His motions became more aggressive with each pump of Tanya's body into the cock. Eventually, the large trans woman grabbed him by the wrist and looked down at him.

"Why don't you put that mouth of yours to good use" she winked.

Danny nodded and knelt down right in front of Tanya's massive cock before shoving the tip right into his mouth, and not making the same mistake as last time, he didn't try to shove the entire dick in one gulp.

Tanya cooed and returned to fucking herself on the dildo which provided the thrusts Danny needed to suck on her dildo, and he didn't need to move his body at all. Danny was getting more and more gulps of Tanya's dong with each pump of her ass into the cock.

"Oh, good girl" Tanya cooed, playing with her tits. "I want you to drink all my cum this time"

Danny nodded and blushed as he continued to suck her dick. There was something humiliating sexy about Tanya calling him a girl while he sucked her off but he was sort of getting off on it. He didn't seem to mind being used by his trans classmate.

Tanya was starting to feel that sense of getting close but wanted to hold off on her climax. She was enjoying watching Danny sucking on her dick, and despite his inexperience was actually pretty good at it.

But, as much as she enjoyed the attention to her cock, the dildo inside her ass was making it impossible to hold back the urge to shoot her load into Danny's awaiting esophagus. She put her hands on the back of his head and slammed his face onto her dick.

Danny gagged as it was in so deep, his lips were on her crotch. This dick was much larger than the wall mounted dildo and his mouth was starting to feel like it was bigger than it actually was. But again, he was getting used to it and continued to prove himself worthy of Tanya's little cock sucker.

Danny was now using his hands to fondle Tanya's balls but didn't want to release from her dick without her permission considering her stern tone from earlier. He could feel Tanya's dick was too hard, and some cum was leaking into his mouth. She was close.

Tanya grunted as she kept on fucking her ass on the dildo. She looked down and noticed the hanging hose and grip attached to the dildo. She smiled and grabbed the grip in her hands and looked back at Danny.

"Know what this is?" she asked. Danny shook his head cock still in his mouth. "The bag attached to this dick is filled with fake semen. I love filling up my booty with this from time to time. I'm surprised you didn't cream your tushy, Danny."

Danny looked surprised at Tanya, he sort of wished he did, cause that very thought made his dick hard yet again. That would explain the actual hollowed hole in the dildo's tip. But anyway, Danny shoved his face back down on the cock, wishing he could turn back time and cream his ass with the dildo.

He watched as Tanya put her entire ass onto the cock and squeezed the grip, and shots of fake semen filled her rectum up. She moaned while the juices coated her insides, setting her dick over the edge which was subsequently deep inside Danny's mouth and Tanya pumped a hot load of cum deep down his throat.

"That's it. Swallow all my cum."

Danny nearly coughed it up as Tanya continued the semen onslaught as it filled up his stomach. He started to tear while she shot load after load of creamy cum into his throat. She could see some of it leaking out of Danny's lip. He gulped the rest down and slid Tanya's cum stained cock from her mouth, wiping some dripping semen from his chin. He looked up at the smirking Ebony trans woman above him.

"Good girl" she smiled.

Tanya released from the cock and the cum leaked from her asshole. She had Danny lick up the edible mixture dripping down her leg. She thought about turning her body and farting a load of the stuff into Danny's mouth, but that was too mean, she actually liked the boy.

The two showered the mess off of them and finished up. Danny got dried off first while Tanya took some time, wrapping her hair in the towel when she was finished. "Okay, that was really amazing" Danny nodded.

"Well I'm so glad you enjoyed."

The two stared awkwardly at one another for a few moments. "Um, so, do you want me to stay still? I think everything is through me and I can probably drive now."

"I mean, unless you just wanna fuck all night cause I'm pretty fucking horny and I don't think I'll be able to stop myself from jumping on your ass, but; I really want to keep you waiting, you'll really appreciate it when the time comes" she winked. "Besides, I'm a little rough, you sure you're ready for that?"

"I mean, I could probably handle myself" Danny suggested.

"Then you wanna bend over and spread your little cheeks for my bad boy?"

"Um…" Danny froze. "Maybe some other time?"

"I thought so" Tanya chuckled. "If you're good to drive, then go ahead. But we're still not done with the project, you know that, right?"

"Right, of course"

"Good" Tanya approached Danny, and caressed his cheek. "You're really sweet, Danny, it'll be a pleasure to truly take your butt cherry, and not some plastic toy."

Danny blushed. "I wouldn't have it any other way, Tanya, and thanks."

But she then hatched an idea. "I got it. I'll give you a little something to remember me by, so maybe you can be ready…you know, when the time comes. Bend over the sink" she ordered.

"Okay."

Tanya disappeared into the loft. She came back a few moments later with Danny's clothes, but also with a pink butt plug. Danny could see in the mirror what it was. "Alright, this is something you can walk around in, to keep that booty hole of yours a little stretched out. Maybe you can show me that you care by keeping it in there when we meet next" she smirked.

"Definitely. Shove it in."

Tanya smiled and bent down behind Danny. She couldn't resist shoving her tongue around the rim of his hole briefly before gently sticking the pink plug inside of him. Danny winced while the larger end part was forced through his sphincter, but it eventually made its way inside and closed on the pink base. Tanya gave his cheeks a playful pat.

"There we go."

Danny smiled, and he and Tanya briefly kissed before the boy got dressed, getting used to having a plug in his ass. He bid Tanya farewell and went to his car still in the lot. He made his way home to UCLA, thinking just how long he would have to wait, but was still excited to have a relationship with Tanya…whatever that relationship was he didn't really know, but was happy to have it. And tomorrow would be another day. The only thing he needed to get used to at that moment, was finding a comfortable position to sit on…


	3. Art or Porn? You Be The Judge

**Summary for the Chapter:**

> After their shower romp, Tanya and Danny continue their sexy little project which of course gets increasingly sexual with each meeting, including Danny crossdressing while Tanya finally acquiesces and gives Danny an ass-fucking he won't soon forget!

Danny navigated the unmitigated mess that is Downtown LA and found his way back to campus parking in one of the structures by his dorm. He was once again uncomfortable getting out of his car as the plug up his ass made it a bit uneasy to sit, stand, and walk. But Danny liked it, and in a way he couldn't wait for this plug to be some day replaced with Tanya's cock.

He made his way into his dorm room, a double room with your usual dorky fair, some posters of video games, a couple of video game consoles with a TV, and a small bed. He also had a laptop on a desk. His room was also a bit of a mess with all his clothes. Danny's roommate was often never there, being with his girlfriend most of the time. This night was no exception.

Immediately, after his door was closed and the blinds safely shut, Danny threw off his clothes and looked at himself in his standing mirror. His dick was already hard, even from orgasming twice from his borderline sexual romps with Tanya. He then turned around, sticking his butt out towards the mirror. He turned his head back and was able to see the plug wedged inside of his asshole.

His perverted brain meshed with his photographic brain and he placed his camera on a mini tripod on his dresser and set the timer, he had another rig for his iphone and did the same thing. Once they were set, Danny got back into position and stuck his ass out with the plug clearly visible while his cameras took snapshot after snapshot of his ass.

He was satisfied and saved the photos to his SD card, where he gleefully uploaded them to his computer, containing the graphic shots of Tanya's ass and body for their class. His dick was still hard and Danny used these photos to jerk himself off to. He sent the snapshots of his ass from his phone to Tanya with the message:

'Pretty Spankable? Lol'

While he jerked himself to Tanya spreading her massive booty on her bed, his phone buzzed, it was a picture message from Tanya, a perfect snapshot of her nearly erect cock while she laid on her bed.

'Pretty fuckable too' was her response.

Danny furiously jerked himself off wishing it was Tanya shoving her cock in his ass instead of the butt plug while he fantasized of one day being able to stick his dick into her asshole. He took more photos of himself in a variety of positions and sent them to Tanya getting lewd responses from time to time.

But alas, it was getting later and Danny had to go to class in the morning. Still plugged up he crawled into bed getting a 'goodnight cutie' text from Tanya before he did. Tomorrow would be a new day.

On that next day, Danny went to his various classes and such, the plug still in his ass. He was getting used to walking with it in. It was a usual day for the boy. A usual day except he noticed he shared another class with Tanya, Art History 101. It was a much larger class and he never noticed Tanya being there before. Today however, he did.

The two waved at each other before class began, taking their usual seats far removed from each other, which is probably how they never knew they were in the same class for nearly half a semester.

While the lecture went on, Tanya, who sat behind Danny in class, fantasized the entire time about the boy. She was mentally kicking herself for not wanting to fuck him silly last evening and playing hard to get as a quasi-punishment for using her dildo without asking. She thought she would get as much of a kick out of it as Danny did, but in reality, all she did was give them each a self-imposed cock block.

After class, Danny stuck around and he and Tanya walked through the hallways. "I never knew you took that class" Danny said.

"Likewise. It's kinda funny how that works" Tanya explained. "You never notice a person until you get close to them, then you notice them all the time."

"I totally agree" Danny nodded.

"So uh, is it safe to ask...do you have it in?"

"Never took it out."

"Ooh, naughty."

The two walked together. Tanya couldn't get that thought out of her head. The thought of Danny walking around with a butt plug in his ass and no one was the wiser. It was making her really horny...too horny in fact. Her brain hatched an idea.

"What do you have to do today?" she asked him.

"Nothing, why?"

"There's an old check cashing place on Sunset over there by Schrader in Hollywood? Meet me there at five o'clock today" she smiled.

Danny smiled too. "I'll be there."

"Good" Tanya gave him a light kiss on his forehead and off she went.

Danny spent the rest of his day wondering what exactly the two would be up to behind this new location? He figured it would be something sexual in nature and also figured it would be semi-public considering it was outdoors, but Danny wasn't too worried about that...in fact it was a turn on for him.

He braved the Westside traffic to get to the location early. It was in fact, a rundown and derelict check cashing kiosk which in its other former life was clearly some type of fast food restaurant near the cross streets of Schrader Boulevard and the famous Sunset Boulevard, of course it wouldn't be famous in this part of town.

Danny got there first. One had to brave an alleyway entrance at the back of the boarded up building where were two graffitied dumpsters also behind it. Danny paced around, his dick hardening from the anticipation. After some more waiting, Tanya showed up in her car. She emerged, with a Victoria Secret's bag under her arm. Danny was greeted with a kiss.

"Hey, what's that?" he asked.

"For you" Tanya winked. "Follow me."

The two walked behind one of the dumpsters, coupled with the retaining wall next to the opening, and their haphazardly parked cars blocking it, no could really see what they were doing. There were a few apartment buildings nearby, but the one next to the check cashing place had a lot of its windows boarded up. The two had multiple blind spots to the streets to block any prying eyes.

They went behind the dumpsters, as they were not filled with trash, there was no horrid rubbish smell. "Lean against the building" Tanya ordered.

Danny did as he was told while Tanya got right behind him. Danny could feel Tanya's bulge rubbing against his backside from under her tight fitting jeans. She slowly pulled his shorts and compression shorts down, revealing his unshaven and plugged up ass.

"Ooh baby" she cooed. Tanya leaned in and kissed both of his cheeks before spreading them out and playing with the plug.

Danny winced pleasurably as he leaned on the warm stucco sided building, hoping now was the time for Tanya to ram his asshole with her dick. His nearly erect cock was almost touching the siding, so Danny leaned back more, which only made this more seductive.

Tanya then got something out of the bag, a Sharpie marker. "Hold still" she ordered.

On Danny's right cheek, in her best handwriting she wrote: BUTT SLUT IN TRAINING. Danny figured she would be marking his ass as a brand, which greatly turned him on.

Tanya had her phone and camera out, first taking a selfie with Danny's ass. Then she got out her actual camera and started to snap away while Danny was in a very lewd and publicly humiliating pose. In a sense he hoped a couple of female police officers happened upon their little escapade and decided to dominate the both of them sexually.

Tanya had Danny do several shots of him having his face against the siding while spreading his cheeks out so she could get pictures of that too. After she was satisfied with this, Tanya got something out of the bag, a black lacy thong which she slipped over Danny's legs and moved them over his hips.

"A thong?" Danny asked.

"I thought that'd be pretty sexy, wouldn't you agree?" Tanya asked.

"Absolutely" Danny nodded.

Tanya once again took more shots of Danny's ass. Danny blushed at the humiliation of having his ass out while wearing ladies underwear but he loved every bit of it. Tanya had him have a hand move the thong out of the way to get a shot with the butt plug.

"Good, now tease that thong and shake that booty for me."

Danny did as he was told. He slowly moved the thong down and shook his ass for the camera. Again, Tanya was satisfied with his shots. She grew closer to him, and pulled her own pants down, her nearly erect dick flopping free. She positioned her tip against the base of the butt plug on Danny's ass and pushed a little bit, causing Danny to moan, hoping she would move the plug out of the way and just pound his ass.

Instead Tanya whispered in his ear. "There's an address in the bag, along with instructions, meet me at that address tomorrow at two" she said before kissing his ear. "And don't move until I leave" she commanded.

Tanya pulled her pants up and moved to her car before driving away. Danny waited at least a few minutes even after knowing Tanya had left. He pulled his pants up, and took the bag to his car. He looked inside and dumped the contents on the passenger's seat. It was a lacy sheer night dress lingerie tank top, and a pair of matching fishnet stockings. Danny also assumed he was to wear the thong. On the note inside the bag it read for him to wear these clothes, and the address was off of an alleyway in the Silver Lake neighborhood, a hipster's ironic paradise.

Danny was a bit skeptical, a thong was one thing, but this was an entire outfit. His skepticism, however was placated by a rock hard dick from being used and publicly humiliated by Tanya and despite any reservations, he wanted more.

Obviously he couldn't wait and tried the clothes on in his dorm. He looked at himself in the mirror and was very happy with his appearance. He blushed when he got a look at what Tanya wrote on his ass in permanent marker, hoping to finish his apparent training. Danny was impressed how Tanya guessed his size as everything fit so perfectly. He took some photos of himself and sent many of them to Tanya, who was very impressed.

The next day, Danny gleefully dressed in his outfit and sped over to the address. It was again between two unused businesses, where Tanya had moved a few dumpsters to block the alley from anyone seeing their activities. Danny was surprised Tanya had even roused the homeless who usually populate these alleyways.

Tanya had a blowup air mattress in the middle of everything. She was wearing a very revealing two piece bikini, the bottom barely containing her dick when she saw Danny. "Hey you" Tanya said. "Look at this cutie."

She groped his ass cheeks when he sauntered over to her. "So, what first?" Danny asked.

"Let's get the boring photos out of the way" Tanya suggested, holding up her camera, as well as a tripod. "Then we can get to the fun" she then held up a pink vibrator, instantly making Danny go erect inside the thong.

Danny started by taking photos of Tanya. They were tasteful, many of her posing in her bikini. Some where her making a surprised face when she would drop her thong under her ass, while others had her laying on the bed with her legs fully extended.

Then of course there were the photos of Tanya simply bending over and spreading her cheeks, and a few of her dick sticking out the side of the thong. After Danny filled up one SD card, it was his turn.

"You're up" Tanya said.

Danny did similar poses. He was blushing while Tanya took his picture, slightly sexually embarrassed as he was dressed in drag. His dick was fully erect and dripping, he literally had to stuff it under his legs at one point.

While he was bent over and spreading his cheeks, Tanya was stroking herself, he still had her permanent marker brand clearly visible on his ass. She was satisfied with the photoshoot. "I think we have enough...for now" she cooed.

"Sooooooo?" Danny asked.

"So, time to start training" Tanya smiled, holding up the vibrator. "You gotta crawl before you can walk, and your tight little ass just isn't ready for me yet...but we can get it there. Get on all fours on the bed."

Danny glibly took the desired position on the bed. Tanya got behind him, first taking a bottle of lube she brought with her and drizzled it on the cock. She then slowly removed Danny's butt plug, moving the thong down over his ass.

Danny winced after the plug was removed, he only done so to clean it, relieve himself, or clean his hole in general. Tanya watched his asshole gape before she slowly inserted the vibrator. There was some resistance, but his rectum being stretched from wearing the plug made it easier to slick itself inside of him.

Danny groaned happily while Tanya got the vibrator inside him an inch or two at a time, after it was all the way in, Tanya thrust it in and out a few times before turning on the vibrations, and Danny almost came instantly.

"Oh, fuck!"

"Yeah, that'll happen" Tanya chuckled.

She continued to fuck his ass with the dildo. Danny spread one of his cheeks apart with a hand to help it glide easier. He huffed while Tanya fucked his ass with the vibrator. He was almost ready to cum.

Tanya could see his ass puckering from the constant dildoing. She would take it out from time to time and watched Danny's lubed up hole gape before going back in again. She still had a few more things to do with her new toy. She took the dildo out and set it aside.

"Alright, now lay on your back."

Danny did as he was told, and laid down. Tanya pulled off her thong and set it aside before straddling her giant booty over Danny's face. Danny knew where this was going. Tanya cooed.

"Take a deep breath" she warned.

Tanya sat her massive ass down on Danny's face. The boy quickly shot out his tongue and rimmed Tanya's hole. It was definitely sloppy at first as Danny was not used to this, but he slowly came around.

"That's right, clean my asshole" Tanya moaned. She got up for a moment so Danny could take a breath. "Like that?"

"Hell yeah!" he panted.

"Good" she sat down on his face again.

She shook her ass while sitting on Danny's face. Her attention quickly moved over to his cock, which had filled out in the thong. Tanya took her hand and started to stroke it, knowing it wouldn't be long before Danny shot his load.

"Ooh, you're good at this, Danny" Tanya chuckled "Really good."

Seeing his dick leaking, Tanya got off the boy again. "What's wrong?" Danny asked, assuming he had done something.

"Nothing. Kneel on the edge, and shove this in your booty hole" Tanya said, handing the vibrator to Danny.

He got on the edge and rammed his ass with the dick. Tanya laid on her back right below his cock. She took it in her mouth and sucked it. Danny winced while he fucked himself. He was ready to cum.

"Tanya...I'm gonna...g-gonna..."

Danny instantly shot his load in the back of Tanya's throat. The experienced trans woman drank all his juices until he was bone dry. Danny let his cock fall out of Tanya's mouth and she licked up some residual drool and cum.

"Now it's my turn."

Danny took the vibrator out of his butt. Tanya ordered him to kneel in front of her very erect cock. Danny was now pretty experienced in the art of dick sucking, and immediately started to chug down Tanya's huge dong.

"Ooh, good girl" she cooed, rubbing head.

Danny threw his hands onto Tanya's ass and grabbed two fistfuls of cheek, making Tanya wince and almost cum. She looked down at Danny chugging her cock in this back alley and was pleased with herself, this was probably the best school project ever, even though half of their shots they probably couldn't even submit.

Very horny, Danny got brazen. He took two of his fingers and moved them underneath Tanya's crack, he slowly inserted them into her asshole. Tanya bit her lip but smiled. "ooh, oh that's naughty. I love it!"

It was so hot in fact, Tanya was already leaking pre cum. She enjoyed this double trouble of pleasure and spread her cheeks while Danny fingered her. He was aggressively chugging her cock, almost having the entire thing in his throat.

Tanya winced while She looked at Danny. Her dick was wet, her asshole fingered, she was about to cum. Without much warning, only with some moans, Tanya finally gave in and released, shooting waves of creamy cum into Danny's throat before she pulled out and let the last few shots land on his face.

"Not quite the money shot I wanted, but still good" she cooed, taking a picture of Danny's face.

The two cleaned themselves up and loaded all the things back into Tanya's car. She had another present for Danny, this came from a male lingerie store. "Got one more thing for you" Tanya said.

Danny studied the item and blushed. It was a banana hammock, basically a jock strap with a patch over the front for the dick, essentially a male thong. Danny blushed. "Whoa."

"Start wearing that when we have our photo sessions. Come to my place tomorrow around five" she gave him another kiss and the two left their seduction alley.

Over the next few days, Danny went over to Tanya's loft and the two would engage in one part taking photos, and the next part, having varied sexual encounters.

Sometimes Tanya would dildo Danny's bottom in many positions. Sometimes he would be plugged up while sucking Tanya's cock or licking her asshole. Other times he would be training his ass on her wall mounted shower cock.

Sometimes Tanya would restrain Danny while he was having various phallic objects wedged inside of his rectum. He came on command while having his arms and legs bound with a ball gag in his mouth while Tanya slapped his balls, and he bounced his ass on a free standing dildo. Sometimes she even spanked Danny's ass while the plug was inside of him.

But the two were in dire need to meet asshole with dick. Tanya slowly came to the realization that Danny was ready for her, but she just wanted to make absolutely sure...plus, it was so much fun to anally humiliate Danny for her amusement. And Danny would agree.

One day, the two had finished another day of shooting, and figured they had plenty of material for their project. Danny had his clothes back on but was about to leave. Tanya was especially apprehensive of him going. Her horniness over the course of this project grew to such a degree that she couldn't wait anymore.

"Well, I'll uh, see you tomorrow? Same time?" Danny asked.

"Yeah, sure" Tanya nodded and gave him a kiss goodbye.

Danny left her and walked out into the hallway. Tanya sighed, she didn't want to wait anymore. In her mind she thought it was Danny now playing hard to get, and she didn't want to waste any more time. He was ready for her...whether he actually was or not. She threw on a robe to cover her naked body and ran out her front door. Danny was in the hallway about to get on the converted service elevator down to the parking structure.

"Danny, wait!"

Danny stopped, hoping this was it. "Yeah?"

Tanya sighed. "Can you take it?"

His eyes brimmed. "Hell yeah!"

"Then get the fuck in here so I can pound your skinny ass!" Tanya ordered.

Danny ran right back and inside the apartment. Tanya closed the door and dropped her robe, her cock fully erect. He jumped into Tanya's arms and the two made out while Tanya started to undress Danny's lowers. His dick as hard too underneath the banana hammock.

"Take it all off and lay down on the bed." Danny tore off the rest of his clothes and jumped on Tanya's bed while the larger trans woman dripped lube onto her cock. "Lift up your legs. Trust me, this'll make it easier" she promised him.

Danny lifted his legs up, revealing he still had his plug in his ass. Tanya immediately took it out, replacing the rim with some cold lube before putting her tip against his hole. "You ready, for real?"

"Fuck my ass, Tanya!" Danny begged.

"I will."

Tanya shoved her tip against his sphincter, getting some understandable resistance as it was pretty tight and Tanya was very large. She slowly got her tip inside after many winces from Danny. He remembered his training and was patient.

Eventually, Tanya shoved her cock inside of him, getting a few inches in at a time in order not to split his rectum wide open. Danny groaned and blushed while Tanya started to pound his sissy ass.

"Oh God!"

"I told you, I'm big."

"I love it so much" he huffed.

Tanya stuck her large cock in and out, slowly building up more of it inside of Danny an inch or two at a time. Danny spread his cheeks out wider and lifted his body back and that's when Tanya slid the rest of her cock inside of him.

"Oh yeah! Perfect" she moaned.

"You're so huge!"

"And you're so tight! God I love virgin booty so much!"

Tanya continued to pound away at his ass, picking up her pace as she pushed herself into Danny's asshole. Danny started to moan louder and louder and Tanya was pleased how high pitch it sounded.

But she wanted more. Tanya was a pretty strong woman and Danny was very light and spindly. She grabbed him from behind and started to lift Danny up, not even needing to take her cock out of him in the process.

"Oh God!" Danny moaned.

Tanya smiled and she moved her hips up and down, fucking Danny while standing up. His ass fell naturally onto her cock. Tanya had her hands gripping Danny's ass cheeks while she fucked him, the two locked eyes.

"Fucking kiss me!" she ordered.

The two shoved their faces onto one another, their tongues familiarizing themselves with the other's mouth. Tanya made her motions more gradual so they could make out easier. Danny released for a breath and stared into Tanya's eyes.

"You like being my little sissy butt slut?" Tanya asked.

"Fuck yeah!" Tanya moaned. "I want more! I need more!"

"Oh, you'll get more baby. I promise you!"

They went back to making out. Tanya picked up her rhythm while Danny threw his arms over her shoulders and ran his fingers through her hair. Tanya continued to impale the boy with her cock. She was gradually getting closer as this was exactly what she wanted. And for that matter, this was what Danny craved.

But Tanya wanted to finish strong and her arms were starting to get tired. She lifted Danny off of her cock while it and Danny's hole dripped in lube and pre cum. Tanya dropped Danny and bent him over the bed with his ass sticking out. Tanya pulled his banana hammock down and over his ankles. Tanya stroked herself.

"Spread them, bitch" she huffed.

Danny did as ordered, his hole gaping from taking it in the ass constantly. Tanya lined her cock up and shoved it back in. "Oh, you're such a slut" she moaned. "Your hole takes it right in. Shit!" Tanya laughed as she got her dick all the way into his ass instantly.

The two moaned while Tanya picked up the pace and vigorously pounded Danny's ass. Danny smiled form the blush of finally losing his butt cherry...well, at least, losing it to a real dick, that is. He was practically drooling on Tanya's sheets.

"I hope you like bending over and taking my cock" Tanya moaned. "Cause you're gonna get stuffed with this bad boy every day"

Danny loved the sound of that. "Oh fuck yeah! Oh fuck me!"

"I hope you liked that sissy outfit too. Cause I'm gonna start dressing you up like a little slut. You want that?"

"Yes! Oh yeah! I wanna be your little bitch, Tanya!"

"You're already my bitch!" she reminded him. "I got some hot friends! I'm gonna pimp this ass out!"

"Oh yeah! Yes!"

"That's why I call you a girl when we fuck" Tanya claimed, spreading his cheeks out with her hands. "Little sissy girls take cock, you understand?"

"Oh yeah, oh yeah, oh yeah!"

Tanya looked down at her sheets. Danny had cum from the constant prostate stimulation. Seeing this, she was close too, especially pronouncing all the humiliating things she was gonna do to him. Tanya's dick throbbed. She shoved the entire length inside of Danny.

"Ready for my cum, slut?" she asked.

"Oh yes! Fuck! Fuck! Fuuuuuuuuuuck!"

Tanya gave one last grunt before her dick shot a massive load into Danny's ass, filling his rectum up with her juices. Tanya cooed and moaned while her cock emptied itself inside of Danny's butt pussy. Danny drooled on Tanya's sheets, lost in sissy heaven.

Tanya gave one last huff before sliding her cock out of Danny's ass, it was coated in her own juices. She let the last few drops fall on top of his cheeks, namely the faded brand she wrote on his cheek days earlier.

Danny's hole contracted and gaped with a river of semen leaking out and falling onto his ball sack. Tanya liked the look of that and grabbed her camera. "Stay there, don't move. Just spread those cheeks out" she ordered.

She ran to get her camera and the marker as Danny spread them out. She crossed out the IN TRAINING with an 'X' leaving only BUTT SLUT. She took a few photos of Danny's red and spent ass as her cum cascaded out of his hole, onto his balls, and dripped onto the floor.

"Now that's a money shot" she moaned. "How do you feel?"

"Sore...and full" Danny chuckled. "But good, though."

"Perfect."

They cleaned themselves up while Danny went to the bathroom and blasted the rest of Tanya's cum into her toilet, he was pleased with himself and the new slut he was about to become...but he was most excited about their project, which was certain to be a success.

They and finished their spread, and dropped the photos off to Len the following day. "Thanks you two, you guys got so many shots" he commented, looking at the stack.

"We hope you like them" Danny nodded.

"And we want a few in the showcase as well" Tanya nodded.

"Great. I guess I'll put you both down for not taking the final. Nice work, I'll see you in class tomorrow." He nodded before the took left him.

Tanya and Danny walked together through the hallway, each had a hand on the other's butt. "So, you ready for your ass tattoo?" Tanya asked.

"Fuck yeah."

"Good."

"You think Professor Hardesy will think they're too much?" Danny asked.

"Nah. He was the one who wanted us to push the envelope anyway." The two chuckled and left the building.

Inside, Len was drinking a coffee and started to go through their photos. He immediately did a spit-take after seeing the first one. It was a photo that was clearly on a timer. It showed Tanya and Danny laying with their face down and asses up on Tanya's bed, their rear ends completely exposed.


	4. Close-ups and Crossovers

**Summary for the Chapter:**

> Danny and Tanya run into an old friend of the latter and are quickly enthralled in the world of erotic photography but Tanya must keep Danny away from a semi-familiar face who wants to seduce him.

**Notes for the Chapter:**

> So, I establish in this story that my three tranny stories "New Gurl In Town", "Fetish & Fantasy", and "Money Shot" are set in the same universe. If read in chronological order in universe, New Gurl In Town happens first, followed by Fetish & Fantasy, and then Money Shot.

We return to Los Angeles, California. The place where movies used to be made, now relegated to the proverbial ashes of its once former glory. We'll pick up where we left off with Tanya and Danny, you remember those two, right?

Tanya was the hot, tall and thick bombshell tranny with a huge cock, thick booty, and big boobs. Danny was her...meh, I guess you could call him her boyfriend. He was lanky and skinny, with a nerdy dirty blonde haircut and glasses, with a small-ish dick and a bubbly feminine ass.

If you recall, the two had just finished their school project which took a turn for the sexual and started them on this sensual path. Danny had become addicted to taking it in the ass, especially by Tanya. He quickly submitted to this super-hot tranny and she loved every moment of it.

The two were getting Danny a tattoo on his ass as a brand to permanently remind him he was property of Tanya. Inside a tattoo parlor in West Hollywood specializing in very personal ink in very personal places, Danny laid on a folding chair in a back studio, it was the kind of chair you find in a psychiatrist's office but could be folded down like a bed.

Danny laid on his stomach with his pants down and his ass sticking up. The tattoo artist named Jane Wittenberg, had shoulder length brown hair with purple highlights in it and proudly displayed much ink on her arms and legs, and possibly elsewhere, as well as many piercings. She was short but very muscular, with really thick hips, a small gut, but large boobs with muscular arms.

Jane wore her nitrile gloves and readied a needle while she looked at the tattoo's design on a piece of paper held up by Tanya. "Yeah, it can be done in one session" Jane nodded. "But, it'll take at least an hour and a half, maybe two."

"That's fine" Tanya nodded, handing Jane the paper. She then whispered into Jane's ear. "If he's a little bad boy—" Tanya said before giving Danny's butt a pat. "Don't be afraid to punish him."

Jane smiled. "Oh, it's one of these clients, huh?"

"What were you expecting from that tattoo?" Tanya asked.

"Thought he lost a bet. But, you're a good customer, Tanya, I'll get it done" Jane nodded.

"Good" Tanya then walked over to Danny's face and knelt down, rubbing his head. "I'll be right out here, sweetie."

"Okay" Danny smiled before Tanya gave him a lip kiss. She then walked out and closed the door behind her.

Jane got out the ink she needed before setting the paper up next to Danny on a stand, similar to what you'd use in an orchestra. "So Danny, we're gonna get very personal over these next few hours..." Jane smirked, getting her needle ready.

Tanya sat outside in the waiting room and thumbed through a dog eared People Magazine that was about four or five issues ago. She looked at the other artist's studios outside the private booths, some had clients they were working on while others were waiting.

Tanya looked up as a woman entered the shop. She was Hispanic and about in her early forties or so. She had wavy light brown hair matching a tan complexion. She wore a white turtleneck sweater with a long matching white skirt with white shoes and to match a white Gucci purse.

"Harriet!" Tanya put down the magazine.

"Tanya! Come here girl!"

The two supposed friends embraced for a hug and kiss. "Did you send another customer to Jane?"

"Yeah, but this one's really personal. Got myself a new boo."

"Ooh, we'll I'm here touching up my latest project, so spill that tea" Harriet insisted.

"You first, Hari. What's the ink?"

"I'll show you" Hari, her nickname, dropped her purse and tore off her turtleneck, revealing a pink bra with C-cup breasts attached to them. She turned around revealing a full back tat, partially finished. It looked like a large dragon fly but was covered in armor, with its many legs holding some form of melee weaponry. Tanya raised an eyebrow.

"Interesting."

"I've always liked dragonflies, plus I started it when I was drunk and I'm too far gone to stop now" Hari turned to a male tattoo artist right next to the waiting area, "Paolo, make sure I'm facing my friend, she's got tea to spill" she said, sitting at the man's chair right by Tanya. He started to ready his ink gun as his station had already been disinfected.

Hari faced Tanya, who leaned on a chair against the small divider separating the waiting room and tattoo area. "Who's the boo?" she asked.

"Barely legal" Tanya smirked then mouthed: "He's eighteen."

"The real question is: who is bigger?" Hari asked.

"Come on now" Tanya chuckled.

"Was he hard to break? I'm guessing he was a virgin, right?"

"Total virgin...in a way he still is" she winked. "I'm gonna surprise him next weekend, let him get a crack at me, if he's a good boy. It's our first month-i-versary together."

"You've trained him well, huh?"

"Such a little slut. But he's so sweet, ugh, he follows directions, he's funny, we love photography; I'm in love, girl" Tanya swooned. "You gotta see him, he has an ass begging to be fucked."

"Ooh, he have any shame?"

"Not really" Tanya went over to her purse and pulled out some unused polaroid's from their projects. "Check these out. I know it sounds freaky, but this is for a school project."

"Oh yeah, I remember you saying you went back to school."

"Best decision I ever made."

While Hari got her tattoo done, she scanned through the photos from their nude impromptu photoshoot in Silver Lake where Danny was dressed like a girl and got his face smothered by Tanya's massive ass.

"Look at that tush."

"Right? He's such a cutie. Oh, how's that thing you were doing with Svetlana?" Tanya asked.

"Already launched. It took us forever to find a flagship model but good ol' Lana, found one off the street."

"Homeless?" Tanya asked.

"No-no, he was a driver or something—that chick needs to get to a car, I swear to God. Does uh—"

"Danny."

"Danny, right; I'll remember that. Does Danny want to...make a little extra money?" Hari asked.

"I'll ask him, but I'm not gonna force that on him. I don't mind sharing him but I wanna be there too, I feel weird pimping him out for money."

"What if he's into it?" Hari asked.

"Like I said, I'll ask him, but I don't know how I feel about it to be honest" Tanya then whispered "These girls get tested?"

"We require it" Hari assured her, and then looked through the photos. "Got any good money shots?"

"Girl, I got just the one" Tanya got a photo from her purse she had personally viewed many times. It was the shot of Danny after his first creampie from Tanya—also subsequently his first real time taking her dick in his ass. Hari smiled as she looked at the boy's bum with jizz cascading from his hole, she also noticed the BUTT SLUT marker on his cheek. "Damn that's so hot. That gonna be his tattoo?" she asked, Tanya smiled.

Inside the office studio, Jane was hard at work sculpting a permanent brand onto Danny's right ass cheek. She had wiped away some excess ink and was refilling the inkwell as she was running low. Jane was getting pretty hot watching the eighteen year old's tush at her mercy and was looking for any excuse to punish him as per Tanya's laissez faire suggestion.

Jane fancied herself a wannabe dominatrix, particularly with men where on the flipside she found herself particularly submissive with women, being bisexual. She didn't want to merely take Danny for nothing but waited for a reason.

At times, Danny would wince and clench his ass cheeks while she would continue to tattoo his butt, and this provided Jane the excuse she needed. After he winced again, she raised her free hand to come down hard on his unused left cheek. Danny ooh-ed.

"You'd better stop your complaining" Jane warned. "I'll have to get Tanya in here."

Danny turned slightly and smirked as if he would like that, but in reality just kind of wanted to be punished. "You can't do it yourself?" he mocked Jane.

Saying nothing, Jane smacked his left cheek hard again. "Don't test me" she warned.

She continued to tattoo Danny's ass and the boy winced again, but audibly louder this time, just enough for Jane to really hear him. She stopped and put her pen aside in a sterile sleeve before walking over to Danny and cupping his chin. "Is this how it's gonna be?" she asked. "Hmm? You want me to punish your naughty ass?"

Danny simply shook his tushy which was enough of an answer for Jane. But of course, Danny didn't know when to keep his mouth shut. "If you call smacking one cheek and giving me idle threats punishing my ass..." he trailed.

Jane took the bait. She smacked him in the face and sauntered over to a standing closet near the other wall and took out a few things, namely a ball gag, some handcuffs, and a strap-on harness and cock. "Fine, why don't we test just how much of a butt slut you are."

She pounced on Danny shoving the gag into his mouth before attaching the belt around his head. She made quick work of handcuffing his wrists behind him before sliding the harness over her legs and onto her hips.

From a drawer, she grabbed a bottle of KY jelly and lubed up two of her fingers. She walked behind Danny and lubed up his hole with her digits before slowly inserting both into his asshole instantly. It took some resistance but the lube helped slide them past his sphincter.

"You do have a slutty ass" she smirked, gliding her fingers in and out of him. "Look how easily my fingers just go in and out of your little butt pussy."

Danny happily moaned while Jane aggressively shoved her fingers in and out of his ass, and it wasn't long before she stretched out his hole for a third finger. Danny groaned as his rectum stretched out.

"Yeah, this is much closer to Tanya's cock, isn't it?" Jane asked, Danny nodded.

The greasy lube dripped down onto Danny's balls while Jane was two fingers away from fisting his hole. She slapped his left ass cheek while occasionally using her free hand to lube up her strap-on for Danny's impending pegging.

"Ready for my cock, slut?" she asked.

Danny moaned under the ball gag, drool escaping his lips and onto the surface where he lay. Jane pulled her fingers out and Danny's asshole immediately puckered and gaped. The wannabe dom wasted no time resting the tip against his sphincter before slamming it inside, meeting little resistance as he was very lubed up from before. Danny blushed while he laid helpless to Jane's cock destroying his ass in this most public of establishments, but he didn't care, and he drank all the attention up.

"I think I'm gonna give you another tattoo, on the house" Jane smirked. "Just to prove exactly what kind of s little subby slut you are" she moaned, pounding Danny's ass.

Danny moaned while shaking his ass to match the rhythm of Jane's thrusts, hoping Tanya would stop by and replace the ball gag with her large cock. Little did he know of the plans Tanya actually had for him.

While he and Jane continued their naughty romp, Tanya and Hari sat by one another while Hari continued to get her tattoo from the surprisingly focused tattoo artist as he would have had a perfect view of Hari viewing the very personal photos of Danny and Tanya.

"So look, you may be apprehensive about pimping him out for cash, but, are you both interested in say...photo work? It's not like you both don't have the experience."

"What kind of photo work?" Tanya asked.

"Well, Lana doesn't know this yet, but I'm looking into branching out, starting my own magazine. Something in the vain of the website without the pimping" Hari explained.

"Like, erotic photos?"

"Yeah, right up your alley. You two can spread those cheeks for my photos. I'm really trying to keep it specializing in transwomen fucking sissies or a transwoman fucking another transwoman."

"But tasteful?" Tanya half-joked sarcastically.

"Exactly. You don't have to worry about fucking strangers and still make bank. Come on, I know you were really into this back when you were filming porn for us, this is photography, but again—"

"Tasteful" Tanya nodded, finishing Hari's sentence.

"Absolutely. Look, at least come to the studio for test shots. If they're good we can go on location, then actually shoot scenes. Maybe we can branch out to video someday. Think about it" Hari finished.

Tanya thought for a minute, this would be an incredibly hot opportunity. Tanya put up a finger to establish she needed a minute. She went over to the back and over to the closed door to the studio with Danny's tattoo. She looked through the window of the door and saw Jane having the restrained Danny getting his asshole pounded by her strap-on. Tanya smiled and playfully shook her head. She walked back over to Hari.

"How's next Wednesday sound?"

"Perfect" Hari clapped her hands. "Give me his dimensions I'll get him some outfits."

"No problem."

"And I'll see you both next Wednesday at three?"

"Sounds good" Tanya smiled. "What about Lana?"

"She'll get her cut. Look if you don't want her touching Danny I'll put my foot down, cause you know how territorial she gets. No boundaries with that woman." She said, Tanya nodded.

"She have a new toy?"

"Yeah, about a year now, he's the reason we have the website in the first place" Hari explained. "He's our flagship model."

"That poor boy" Tanya winced.

"No, he's a little fuck-slut, kind of like your Danny except with maybe even less shame. It's probably for the best, our clients like to date their sissies before fucking them and if he's not twenty-one yet the pool is limited, our clients love the club scene here. Danny wouldn't get half the work the twenty-one plus models get. So, like I said, this magazine is my new pet project, but I'm interested in branching out into video, there's a lot of money to be made in porn nowadays."

"As long as I'm a part of it, I know Danny will be interested" Tanya smiled.

"Good" Hari smirked.

Tanya and Hari then talked of old times good, bad, and ugly while her tattoo got finished and Danny got his tattoo's...after getting thoroughly fucked from Jane.

Later that evening, Danny was with Tanya in her Arts District loft where their project and subsequently their relationship began. Danny didn't go to his dorm much and planned on moving in with Tanya soon as it would be a private place for their sexy relationship to blossom unabated.

They were in the shower. Tanya was busy shoving her dick deep into Danny's throat while the newly tatted boy knelt on the wet bathtub floor and chugged her massive cock, now completely at full length.

"Ooh baby. Yeah, that's it" Tanya moaned. "That's the stuff."

The boy looked up at Tanya with wide eyes while shoving his dick deep into his mouth. He would occasionally stop to spit on it and swirl his tongue around her tip. Tanya did indeed train Danny very well.

"Mmm, I'm close babe" she swooned.

Danny was used to her saying that. That meant he would get a hot and creamy load of cum into his throat. He aggressively sucked on Tanya's dong while using his hands to play with her balls. Tanya bit her lower lip while watching her subby boyfriend get face fucked.

"That's it baby...that's it" she huffed.

Danny shoved her dick deep into Tanya's throat while squeezing her balls, which was all the sensational euphoria Tanya needed to be sent over the edge. She gripped the back of his head and forced it onto her cock.

"Ooh baby! I'm gonna cum! I'm gonna cum!"

And cum she did. Tanya shot her load deep inside of Danny's throat and the boy drank it all up, letting it land in his esophagus. He didn't miss a drop while Tanya emptied her balls inside of his mouth. She finally released, letting her cock pop out of his mouth while the shower water washed the saliva and cum off of it. Danny swallowed the rest and stuck out his tongue to prove he was a good cum dump.

"Good girl. Come here."

Tanya had Danny stand up and she gripped his lower back while the two made out, their wet bodies rubbing together while their tongues explored each other's mouths. Tanya got a taste of herself while she shoved Danny's tongue deep into the back of his mouth. The two released and stared lovingly into each other's eyes.

"Alright, let me see your ink again" Tanya insisted.

"Okay."

Danny turned around and leaned against the back of the shower wall and stuck his ass out, revealing two tattoos for the price of one. The obvious one was the one on his right ass cheek, the reason he went to the tattoo parlor in the first place. It was a heart with pink airbrushing and in the middle in calligraphy was: TANYA'S LIL' BUTT SLUT. But the second tattoo, given free of charge by Jane as punishment for Danny's shenanigans was a tramp stamp just above his ass also in calligraphy which read: CERTIFIED SISSY.

"I can't believe she gave you another tat just to punish you."

"Well I was a bad boy" Danny smirked.

"I know" Tanya swooned and slapped his ass. "And that's just how I like you. You like it?"

"I love it."

"Perfect. Let's finish up, and have a nightcap."

The two finished their shower and toweled off. Now clad in robes Tanya went into the kitchen and made them both a nightcap of neat genuine aged Kentucky bourbon. They both sat at her breakfast nook.

"So um, I need to talk to you about something—nothing bad, actually it might be a good opportunity, for the future possibly" Tanya explained.

"Sure babe, anything."

"While you were getting inked...and fucked, an old friend of mine came in to get a tattoo of hers done up. She's part owner of an adult modeling agency on the Sunset Strip. And, I told you I used to do erotic photos and porn before going back to school, and well..." she trailed

"Well..." Danny shrugged.

"I told her about you, and how kinky we are" she added, and Danny chuckled. "She wants to branch out and do a magazine, about, about trannies fucking little sissy boys like you, and maybe someday doing porn of it."

"Like film porn?"

"Yeah. But I figured you'd at least be into doing some generic photos for at least test shots, and whatnot."

"Why do you sound like you're assuming I wouldn't like that? That sounds so hot."

"I figured."

"Maybe I can help break in as a photographer?" Danny suggested.

"That could be arranged, I'm sure. But you're gonna have to take some dick first, but I doubt you mind that" she said, rubbing Danny's head.

"So, it's a modeling agency for porn?" Danny asked.

"In part. Their moneymaker is a website, my friend, Hari, she runs it with another mutual friend—who you should avoid at all costs" Tanya warned. "We won't be a part of that, just you know, tasteful magazine photos."

"And porn?" Danny asked.

"Maybe. Maybe" Tanya reminded him.

The two finished their beverages and got naked, crawling into bed next to one another, slowly drifting off to glorious sleep. The next few days turned into a week, and it was Wednesday afternoon, the day Danny and Tanya found their way to the modeling agency on The Strip.

They went to a part of the studio that was done up in white for a photoshoot, with many studio lights and several cameras on tripods facing a white backdrop with several white boxes to act as chairs and the like scattered about.

They found Hari who was frantically getting everything set up. She smiled, getting a good look at Danny who was just as eager to get started himself. "Always the workaholic" Tanya chuckled, giving Hari a kiss.

"No more than usual, this is him?" she asked, not used to seeing a fully clothed Danny.

"Yup. Danny this is my old friend Harriet Arciniega. Hari, my special man, Danny Lowry."

"Hari, it's nice to meet you Danny."

"Likewise."

"Alright, well, we got a big afternoon ahead of us, so you and I should get better acquainted cause we are going to get extremely personal extremely soon."

"Let's get started" Danny insisted.

"I like you already."

"Hey uh, where's Lana?" Tanya asked.

"Her office—I think or yelling at somebody, who the fuck knows" Hari sighed.

"I'll be back" Tanya said before turning to Danny. "Now you be a good boy, and do everything Hari tells you" she ordered him.

"I will."

"Good" she gave him a kiss. "I can't wait to see" Tanya then vanished out of the studio. Hari ushered Danny to two chairs near the photoshoot facing one another. Hai grabbed a pen with a waiver on a clipboard.

"Okay Danny, I'm sure Tanya filled you in on the basics, but just so we don't get sued, we gotta get the legal bullshit outta the way."

"No, totally, let's do it."

"Okay, so you know these photos are going to feature you fully nude, will that be a problem?" she asked in a tone striking the both of them as obligatory, as if Danny was gonna say no based on Tanya's description of him.

"Not at all" Danny nodded.

"Thought so" Hari checked a few boxes on the waiver. "You have no problem with the camera capturing your: body, genitals, penis, testicles, buttocks, and asshole?"

"Nope."

"Okay" another few check marks. "Now these are the things that we can take or leave, we can just have you do nude photos but if you want to do more, we are certainly open to that, and you will of course be handsomely compensated the more you consent to."

"Sounds good. Like what?" Danny asked.

"Are you okay with: dildos, butt plugs, vibrators, strap-ons—"

"Don't forget anal beads" Danny winked, trying to be playful, but also to prove what he was up for. Hari smiled.

"Right, of course. You're okay with any of those or other bodily approved phallic object being inserted to your mouth or asshole?"

"Totally" he nodded.

"Good. Outfits, do you have a problem with: thongs, panties, heels, or any other feminine clothing or makeup, or being sissified on or off camera?"

"Not at all."

"Excellent...obviously the big one, this project will feature transwomen fucking men, will there be a problem with you having a transwoman's penis anywhere on your body, or inside your mouth or asshole?"

"Nope, that's why I'm here."

"Perfect, how about licking, kissing, biting, rimjobs, fingering, will you have problem licking vaginas?"

"Not at all" Danny shook his head.

"Good. Restraints? Cock cages, cock rings, ropes, chains, cuffs, riding crops, paddles, gags; any problems?"

"None."

"Okay, any pain to your balls, penis, or buttocks—spankings I mean?"

"Love those!"

"Very good—you're doing great, I know this is very personal; now with semen, you are fine with semen on any part of your body minus the eyes?"

"You bet!"

"Okay, so no problem with facials?"

"None whatsoever."

"Are you okay with licking, spitting, or swallowing semen?"

"Yes."

"Okay, now I probably know the answer to this but are you okay with semen in your butt? No problems with anal creampies on or off camera?"

"Need to prove it to you?" Danny winked.

"No, I've seen a few photos" Hari chuckled. "But I have to hear you say it, legal mumbo-jumbo, are you okay with having both holes filled simultaneously, or being shared by multiple penises"

"Yes I am!"

Good, and now locations, provided there is a safe location are you comfortable with doing all the above outdoors or near a public space?"

"I'd prefer it" Danny smiled.

"I love the eagerness, and these will be crowd controlled of course, and finally, this is sort of a repeat question, are you okay with doing all the above dressed in drag?"

"Absolutely!"

"Excellent, well, you're on your way Danny. Let's get you naked and get started."

Danny happily nodded and started to take his clothes off, not nervous whatsoever. While he wasn't, Tanya was, she walked over to a...seemingly familiar office, and knocked on the door. A thick Russian accent of a woman boomed.

"What you want?"

"It's me, Lana."

"Oh-me who?" she asked with a moan.

"Tanya Cromwell."

She heard a grunt, then a few more moans. "Come in!"

Tanya opened the door, revealing a woman with jet black hair, and a large bosom underneath a pants suit. She was sitting at her desk looking down. The desk clearly hid anything below her belly area. This Russian woman should be familiar to those familiar with my work: Svetlana or Lana. Lana let out one big moan. Tanya stood there and said nothing.

Lana fixed herself in her chair, and a moment later, a head popped up from under the desk, the head belonging to an equally familiar redhead who licked his lips. He stood up.

"Da, you go, Terry."

"Yes, Mistress" he walked from around the desk.

"You have date tonight, clean yourself up, you disgrace."

"Am I Courtney, again?" he asked.

"Nyet um...Lucy, or Sally? I don't know, Harriet give you details, now go" she commanded, he nodded and left. Tanya turned back to Lana who lit herself a cigarette.

"He the one?" Tanya asked.

"Da, perfect sissy slut" Lana said, taking a drag. "Harriet tells me you want back in for photography? Some new bullshit magazine or whatever the fuck?"

"Something like that."

"You have new toy too?"

"He's way more than that, which is why I'm here to tell you, to stay away from him" Tanya sternly yet calmly warned the undaunted Russian.

"He is how old? Can he drink?"

"Not legally, he's eighteen."

"You are what? Mid-thirties? First sign of new woman he leave you, why spoil that?"

"Oh we can swing, but I control the when and where" Tanya insisted. "And he's a good lover, I don't want you fucking with him. I know how you manipulate people, Lana. I bet that other one was taken in by your famous charm?"

"I gave him warning" Lana smirked.

"I'm sure it was vague and ambiguous, which is perfect to invoke curiosity" Tanya scoffed.

Lana took a long drag, blowing the smoke right in Tanya's face. "Sue me."

"Just stay away from him" Tanya said more sternly.

"Hey, if he wants dick, I give him dick. You no control who he wants."

"You're a siren, Lana. It isn't fair. I stopped working for you the moment I saw who you really are."

"And now you want back in?" she said, finishing her cigarette.

"For Hari, not you."

"She owns as much in agency as I do."

"This isn't your project, it's hers."

"I still pop in."

"You can look, but don't touch" Tanya warned.

"You know why we no need condoms in production anymore?" Lana asked, Tanya rolled her eyes, she's heard the story already.

"Because you convinced the board of supervisors—through whatever blackmail you had up your sleeve, to overturn their previous ruling that all pornographic material filmed and photographed in Los Angeles County featuring penial penetration must be wrapped in a condom while inserted into a vagina and/or asshole...yeah, I know; you're persuasive as fuck" Tanya explained.

"Right, if I can convince five busybodies to change mind, I can convince sissy fuckboy to have my cock in his ass"

"This is the last warning" Tanya said getting in her face.

"I look, no touch. But if he interested, I say yes."

Tanya groaned. "I'll guarantee he says no."

"Whatever you say. We finished here?"

"Yeah, we're done."

"Is good to see you again, Tanya" Lana smirked.

"Wish I could say the same" Tanya sighed before exiting. Lana smiled, watching Tanya leave her office.

Outside in the studio, Danny was busy being the subject of the photoshoot. He was completely naked and leaning against the wall of the white backdrop while several camera people who worked for the agency snapped away while bent his tattooed ass over.

He had gotten used to this from his school project and was very comfortable by this point bearing all for the world to see, of course this time it would be viewed in a magazine and not his absurdly opened minded arts professor.

"Good, good!" Hari called. "Alright, bend over just a little bit more for me Danny? Alright perfect! Hold that pose!" Hari then walked over to the redhead, Terry, our sissy protagonist from the Fetish & Fantasy series, fresh from getting an obvious under-the-desk blowjob from Lana. "Yeah no, this one's real easy,actually. She wants you to fuck her" Hari explained.

"Really?"

"Oh yeah, I couldn't believe it either. Same rate and everything. Simple date, go back to her hotel and fuck, you can come as you are there's no clothing instructions either" Hari explained.

"Wow, yeah that sounds good, cause I'm sore as fuck from the last one" he groaned rubbing his posterior. "Thanks Hari."

"You betcha. She's at the Waldorf, Zoey is her name!" she called then turning her attention back to Danny. "Alright, let's get some close-ups of that tushy!" Hari took one of the cameras off the tripod and waltzed over towards Danny. "Okay Danny, now I need you to spread those cheeks as wide as you can" she said already snapping some shots. Danny did as directed, spreading his ass while his well-used hole puckered. His dick was rock hard from exposing himself for the camera. "Good, good-this is good. Okay, alright I think we can get a toy in there now, is that okay, Danny?"

"Absolutely!"

"Good. I need a plug on set."

A PA, largely reconsidering their life choices ran over to Hari with a pink butt plug and a bottle of lube. Hari quickly lubed up the toy and pressed it against Danny's asshole. He grunted while the toy was forced inside of him, but his rectum quickly swallowed it up and only the circular base was showing.

"Perfect" Hari dried off her hands and got right back to shooting. "Spread them Danny, spread 'em, good. Good I like that, now turn your face and give a little pout for me...okay, now try to smile, like you enjoy having a plug in your tush...yes, just like that, very good."

Tanya walked into the studio, fresh from her stern warnings to Lana, where they seemed to fall upon proverbial deaf ears. She smiled watching Danny, now in a bear crawl position with his ass sticking up in the air with the butt plug inside him.

Hari then had Danny sit on one of the white boxes, straddling it with his legs while sticking his ass on it then looking back. He winked after seeing Tanya who reciprocated with blowing him a kiss then giving him a cutsie wave.

She then turned and saw Lana now standing in the doorway of the studio getting an eyeful of Danny's rear end, which made Tanya's warning that much harder for her to obey considering what we know about her perverted nature.

Tanya shook her head at Lana who merely scoffed it off but backed away from the photoshoot already seeing what she wanted, but Tanya knew it wouldn't be the end of that. She had to protect Danny any way she knew how.

After getting more shots Hari turned to refill an SD card on a camera when she noticed Tanya walk in. "Take five, Danny. Great work!" she called before turning to her. "He is eager, that much I know for sure."

"That's good, he's well-trained" Tanya winked.

"How'd your warning to the wicked witch go?" Hari asked.

"Like you'd expect: she politely yet condescendingly said she wouldn't aggressively pursue Danny but you and I both know that's bullshit. Then she said she wouldn't stop him if he asked to be fucked" Tanya explained.

"Well it's my magazine so her input won't hold much weight. We did hire a larger staff so her day-to-day tasks are limited now so unfortunately she'll have more free time to drop in" Hari added with a sigh.

"Well, I'll be around more to police her, just for the love of God, If for whatever reason I'm not around do NOT leave the two of them alone. Danny's so cute and impressionable she will say and do anything to get inside his ass."

"Don't worry, I'll keep them at an arm's length. Her main focus right now is drawing in more investors so those meetings and such have been eating up a good chunk of her time, but when there's no meetings she's literally just here trying to seduce interns and the PA's and especially the talent like she does nothing else I swear to God. Hey, did you happen to see a redhead?"

"Yeah, it was weird he was blowing her, I mean I think he was" Tanya pondered. "Is that the model boy?"

"Yeah, Terry. Lana's personal fucktoy. Good news is, when he's around, she'll get off on him, then she's usually good for most of the day, she'll fuck off in her office and order something pointless from Amazon or play solitaire or whatever; but, when Terry isn't here and Lana has nothing to do, she is a thirsty fuck-hound."

"Gotta keep that boy around" Tanya urged Hari who was fiddling with a tripod now.

"Therein lies the problem. He's been at this for about a year, and he gets a lot of dates. Also, to make matters worse, he's been moonlighting with another agency and it's looking like he may have a future with them, it's erotic, but no crazy tranny bending him over and ramming his ass three days a week. I give him another month, maybe two, so, she'll be looking for a new toy, at least at the office" Hari explained to Tanya's sigh.

"Fuck. They can't just be a thing?"

"They are, but Lana won't tie herself down. It's a power move with her. Yeah, they'll fuck in her mansion but what are they gonna do when he's not there? Terry's too much of a pussy to demand they be monotonous plus he's made a pretty sizable living being pimped out for the past year so it'd be hypocritical and Lana's always trying to feed her beast. I'll give you an example then we get you in with these shots" Hari continued.

"Oh good, I've been waiting for that" Tanya cooed, starting to take her clothes off.

"So, one day a few months back, Terry was supposed to come in to update his shots for the website. He had a pending date and I won't go into the details about how the website works but at the last minute she offered double his rate if he just spent the day with her. He's twenty-two and lives in a studio apartment and up to his ass in student loans so of course he fucking said yes, so he goes, leaving a cock-blocked Lana with her dick in her hand and a bottle of lube in the other, so, what does she do? Without any thought she plucks a random male intern tells him to do some filing in her office—not above of their job description, and I walk in to hand her the month's budget maybe fifteen minutes later and here's the guy, shirt on, no bottoms, Lana sitting on her chair with this guy straddling his ass on her cock—fifteen minutes. No shame, no boundaries, and she has this evil gift where she can pick out the most mentally weak and sexually deprived among the crowd and seduces them like a shot, not saying it's gonna be Danny, but I promise you she'll try" Hari finished.

Tanya, now completely naked, crossed her arms. "And I'll be around to stop it."

"Good, now let's get some shots of the two of you, huh?" Hari asked as Danny was certainly ready for more, not knowing exactly what he was in for in the near future. "Okay, now I want to get a lot of your booty's next to one another, so let's start with some wall leaning and really stick those tushies out" Hari directed them.

Many of these shots were in fact tasteful. Many of them were Tanya and Danny side by side with their butts sticking out for the camera. Some of them would be closeups with both of them spreading their cheeks with their assholes puckering.

"Yeah really good you guys. Who wants to be fucked first?" Hari chuckled.

Other side-by-sides featured them both in the bear crawl position again the focal point was their asses. Some featured them full frontal with their dicks erect and sticking up, some with them both touching.

Other shots featured Danny and Tanya taking turns sitting on a free-standing dildo sitting on one of the white boxes instantly turning them both on. They would occasionally look at the camera making faces.

One of the shots was Danny kneeling with his arms cuffed behind him and the plug back in his ass while he was sucking Tanya's massive cock, which was in the running for the centerfold shot of the magazine...so much for test shots.

But the shot they were both really looking forward to was this: both Danny and Tanya were butt-to-butt while a large double sided dildo was rammed in both of their sphincters. The two moved their hips onto the cock and fucked their own tushies simultaneously.

"Ugh, this is perfect you two, really sell it for the camera, slam yourselves on that dildo" Hari called.

Danny's favorite though featured him with a cock cage around his dick while a ball gag was stuffed into his mouth with handcuffs on his wrists. Tanya knelt below him spreading his ass cheeks where CUM SLUT had been written on his cheeks with a marker in addition to his sissy tattoos.

"Wonderful shot!" Hari said

The last shot was Danny bent on the box on his knees with a gag in his mouth and his wrists and ankles shackled while Tanya had one leg on the box and used a riding crop to spank Danny's ass while it was exposed.

Finally, the two had concluded for the day. They were putting their clothes on while Hari was entrusting all their SD cards to one of the interns. "Okay, this was such a productive afternoon. Let's try tomorrow, I have a location all picked out, I'd really like to see this cutie all dolled up in public" Hari said, Danny blushed.

"Same time tomorrow?" Tanya asked.

"Absolutely, I'll text you the address" Hari nodded.

"We'll be there."

"Thanks Hari!" Danny called.

The two walked through the studio, passing Lana who gave Danny a wink. Tanya quickly pushed him along but perhaps she didn't have to as there was something about her that made Danny very uneasy.

"Was that her?" he asked.

"Yup. Like I said, you need to avoid her at all costs."

"I think I can arrange that."

While they continued walking, Danny looked behind them to see Lana continuing to walk, her ass shaking as she did. Danny gulped, getting a nervous hard on once again. The two left for the evening, more misadventures to come.


	5. Didn't Sign Up For This...

**Summary for the Chapter:**

> Danny and Tanya continue to be part of Hari's magazine with Danny taking it up the ass in a variety of positions and becoming a total sissy. But Lana finally strikes back and puts him and Tanya in an awkward yet sexy situation.

The next day came and it was time for day two, their first official on location shoot. It was actually in the warehouse infested Arts District not far from Tanya's loft. Behind an alley between two ancient brick warehouses is where we lay the next scene.

Unlike the guerilla shoot of their past, this was a professional shoot with multiple cameras on tripods, and studio lights. There was even a Star Wagon trailer to get the two in the proper makeup and outfits.

Tanya went first, now wearing a sexy policewoman's uniform with booty shorts and stockings as well as black go-go boots, tight blue shirt with badge, a hat with aviators, and a belt consisting of handcuffs and a plastic baton.

Then it came time for Danny's turn inside the makeup trailer. Tanya had left and given him a kiss and a pat on the rear before he entered. She looked out towards the end of the alleyway, and there was Lana, observing and smoking. This earned an eyeroll from Tanya who made the 'I'm watching you' motion.

Inside the trailer was a makeup artist, a regular beauty school dropout, as well as Hari. "Okay Danny, we're gonna try some feminization shots today, which you are okay with, right?"

"Of course" he nodded.

"Good, take off your clothes and take a seat, Lexi here is gonna make you pretty" Hari ordered.

Danny was now naked and sitting in the makeup chair, getting some foundation, blue eye liner, mascara and black lipstick. Danny ogled at the outfit laid out on the table in front of him. It was a black sheer midriff, with fishnet arm stockings ending at the interiors of the fingers, an extremely short black skirt which hardly covered anything, a black thong with a pink heart a the strap connector, fishnet stockings for the legs, a garter belt with straps connecting at the top of the stockings, and a pair of black high heels. On a mannequins head with a brunette wig.

"So for this I was thinking you dress as a little sissy hooker, and officer Tanya is gonna come over and "inspect you", so to speak" Hari explained. "Now, how much humiliation do you think you can withstand?"

"Like...baton in the ass, humiliation? I mean, I'm going full sissy bitch, I think the line is crossed" Danny shrugged.

"I like where your head's at" Hari said. She then smirked, and held up a tampon. "But I was also thinking she finds this inside your hole" she said to Danny's smirk. "And were also gonna have you completely in chastity today, too." She held up a pink cock cage.

"Let's get started."

While Danny was busy being sissified, Tanya waltzed over to Lana, now on another cigarette. "What?" she asked.

"You know what" Tanya raised an eyebrow and crossed her arms. "I meant what I said. Danny's mine, and you can't have him."

"I am merely observing" Lana defended herself.

"You think because I haven't worked for your vindictive ass in a while that I've forgotten all your tricks? If I didn't say shit yesterday would you have "observed" or fucked off in your office?" Tanya asked.

"Then why say anything at all?"

"Because I knew we couldn't avoid you forever, and I'd rather say my peace then have shit get ugly later. I know how you are, and I know you're only here to try and steal my man" Tanya deduced.

Lana took a drag of her cigarette and blew the smoke right in Tanya's face, the Ebony tranny wasn't moved, however. "In honesty, I seen enough to know your sissy slut boy is hot. I am here in actuality to film Harriet's little photoshoot to see if film is more viable."

"But see, it's not your project, Lana" Tanya gritted her teeth.

"Da, but is under my company, therefore I have right to see how my money is spent, and I want to see if you and sissy boy would do well for porn."

"Were thinking about it" Tanya crossed her arms.

"You could make real money. Cute fuck boy like that bring in big bucks."

"I said were thinking about it, we need to see how the magazine goes" Tanya sneered. "I don't work for you, I work for Harriet, I don't care if you both have equal stake in the company, it's her thing, not yours. And you just want to do what you do, you want to "test out" Danny, and turn him into one of your zombified boy toy's."

"And you haven't?" Lana asked, flicking some ash and taking another drag. "Tanya's lil' Butt Slut? Certified Sissy?"

"Okay, that second one was not me."

"You are hypocrite" Lana spat. "You have little pussy teen slut wrapped around your cock, how is it different than me? Hmm? Cause I'm Russian? I am cold?"

"Don't you even bring up any of that, you know this can get ugly. I'm nice to him, I like him, I respect him, and he—"

"—He takes it in the ass. You are me with nicer face, nothing more" Lana continued.

Tanya was admittedly speechless after that. She didn't like it when Lana was right, her demeanor was partially responsible for why she left working for her to begin with In her heart she knew Lana was lying. She truly cared for Danny and true, she had a massive booty and his dick lacked in size, but it wasn't like it was non-existent, he was more to her than a piece of ass. Though, she did plan to let Danny fuck her that weekend, it wasn't fair that they didn't do more where she was submitting to him.

"I am not you" Tanya sneered.

"True, you do not live in Beverly Hills mansion and you do not rub elbows with foreign horny businessmen, but you are me. You find cute boy who wants to bend over for your cock and fuck him senseless and make him say thank you for privilege. He ever fuck you?"

"This weekend actually."

"So no? Even I let my fuck boy's bone my ass."

Tanya rolled her eyes, it seemed the argument was once again getting her nowhere. "I'm done with this conversation."

"Cause I am right. Now, I will film photoshoot and use as pretext for pornography shoot in future. And maybe jerk off to it later" Lana smirked, dropping her cigarette to the ground and stomping on it with her foot. "Run along now" she condescendingly shooed Tanya away.

Tanya sighed, accepting the very sad fact that Lana was going to be ogling her eye candy whether she liked it or not. But she smiled as Danny exited the trailer, now a completely transformed sissy slut.

"Well, look at this little hottie" she put the brim of the sunglasses against her nose.

"Cute enough to fuck?" Danny asked.

"You're always cute enough to fuck" she kissed him on the forehead and the two of them walked over to the shooting area, joined by Hari moments later.

"Okay you two, first day of location shooting—yay; um, very simple though, it looks more complex than it will be" Hari explained. "Basically were gonna start with the two of you facing the camera against the brick warehouse, and let's try to get as much of the baton in as possible so Tanya, maybe hold it up for as many shots as you can. Then I was thinking we get a glimpse inside Danny's panties, before you turn him around, do some frisking if you'd like, but obviously were interested in the tushy."

"Do you just want me to go full bend over and butt fuck?" Danny asked.

"No, we can do more, let's get the handcuffs in there, play with his butt if you'd like, Tanya. Then we'll stretch him out, we can get that baton up his hole, that'll be hot, then we can move on to some dick play, maybe some dick in the ass, but I'd like you to finish as a facial" Hari explained. "Sound good?"

"Yeah."

"Totally."

"Awesome" Hari gave them thumbs up. "Okay, first positions, get the cameras ready—it's photos not film but if you'd like to do dialogue it's fine in my book"

Everyone got to their positions while Danny and Tanya leaned against the wall. Tanya had out her baton and started to caress Danny's mini skirt and panties, particularly around his crotch area.

"Alright officer Tanya, move the panties aside...good"

Tanya slid the crotch of the panties to the side and Danny's caged cock flopped free. He blushed, as did Tanya. "Oh damn, and here I thought I found just a regular whore, huh?" Tanya chuckled, trying to find a character to play.

"Just a sissy boy" Danny winked.

"Alright Tanya, play with his caged little dick for a few shots...perfect, just like that. Okay, now spin Danny against the wall."

Tanya woman-handled Danny and forced him to face the wall with his ass sticking out. Tanya ran the edge of the baton all down his back, down to his ass, now exposed as Danny bent himself over.

"Good, good."

"I'm gonna have to search you for contraband" Tanya warned.

"Go ahead" Danny chuckled.

"Great, now Tanya use the baton to get between the panties and yank them down" Hari ordered.

Tanya slid the baton between the light fabric and forced the underwear down to Danny's stocking covered thighs. Tanya laughed when she saw the string of the tampon sticking out of Danny's asshole.

"You little slut. Look at you sticking tampons up your butt."

"You can stick something else up my butt" Danny cooed.

"Alright, Tanya let's get that tampon out of there" Hari said, Tanya pulled the string and the tampon fell out. "Alright, now let's take those cuffs and detain Danny's little wrists."

Tanya took the cuffs and cuffed Danny's hands behind his back while Hari caught the shots from every angle. "Now let's get a strip tease from Tanya, slowly get those booty shorts off."

Tanya made good effort on her little strip tease. She slowly moved her shorts up and down for the camera, finally shrugging them off and showing off her beautiful ass and her rising cock. She slapped her dick against Danny's exposed ass.

"This is good, I like this" Hari nodded. "Okay, let's get Danny on his knees, and get a towel under him, then let's do a rimjob and a little blowjob, okay?"

A towel was placed on the ground and Danny, his wrists still cuffed was forced on his knees, while Tanya's booty was right in front of his face. He licked his lips as he stared right into Tanya's hole.

"Okay, Danny shove that face right in there" Danny didn't hesitate and went right in, his tongue licking around Tanya's booty hole. Tanya cooed as her sissy boyfriend rimmed her. "Good, really shove that face deep in there Danny!" Hari ordered

Danny motor boated Tanya's crack to really drive the point home that he was dedicated to rimming her ass. Tanya moaned some more, grabbing the back of Danny's head and shoving it in deeper.

"That's good Tanya, perfect, shove that face in there!" Hari cooed. "Okay, alright, let's move on to that blowjob, you're both doing great!"

Tanya let go of Danny and immediately spun around and her cock hit him right in the face while Hari captured that moment perfectly on camera. Danny opened wide and stuck his tongue out just like Tanya had taught him and the thick Ebony shemale shoved her cock into his mouth, meeting little resistance.

"Perfect, really sell those thrusts, Tanya. Good!"

Tanya shoved her cock deep into Danny's mouth while he choked her dick down, leaving a slimy entrail of saliva escaping his lower lips and falling onto the towel below him. Danny wished he could use his hands to jerk her off but they were still bound behind him.

"Keep getting it deep, don't be afraid to take baby steps, I want that cock all the way in his throat" Hari called.

But the two were well experienced in blowjobs and Danny knew what to do, relaxing his jaw muscles so the dick would glide down into his throat easier. Hari was impressed with the shots but none of them noticed Lana in the background with her camcorder catching the entire scene on camera.

"That's perfect. Alright now Danny's really been looking forward to the baton buttfuck so let's bend him over and let's get a dildo to stretch him out a little first" Hari suggested.

"No! I can take it" Danny huffed.

"You're sure?" Hari asked.

"It's pretty thick" Tanya said, slapping the baton against her opposing hand.

"Trust me babe, I can take it."

Tanya looked at Hari who shrugged. "Okay, let's get him against the wall."

Danny was bent over the wall once more with his face completely resting against the bricks. He blushed as the wind caused the wig to blow on his more exposed shoulders. His bound wrists were right on his ass cheeks and he spread them out wide while Tanya lubed up the baton.

"Okay bitch, I'm gonna have to inspect you for more contraband" Tanya said, still in character.

"Oh yes! Fuck me with that big thick baton" Danny begged like the slut he was.

Tanya rested the tip at his sphincter which puckered immediately. She tried again and forced it in while Danny moaned like a girl. Tanya again recoiled as his hole gaped slightly, before trying a few more times.

She finally got it past his opening and slowly inserted a few inches of the baton at a time while it was recorded and photographed. Hari was getting pretty hot herself from snapping the close-up photos.

"Oh that's good. That's so hot you guys" she cooed.

Tanya increased her speed as the baton was lubing up Danny's rectum. Danny moaned louder and louder as Tanya fucked his ass with the fake club. Danny used his bound hands to spread his cheeks out wider to better accommodate this new anal invader as his ass ate it up.

"That's perfect!"

Tanya picked up speed, now using her free hand to keep herself hard, still a bit moist from Danny slobbering all over it mere moments ago. Danny continued to blush as his face was completely against the warm brick building enjoying getting a humiliating ass pounding from the business end of the baton.

But he truly wished he was getting a big fat load in his ass from Tanya's massive schlong. "Please officer. Please fuck me with your big meaty cock" he begged.

"How bout it, Hari?" Tanya asked.

"Go for it, make that bitch sing."

Tanya pulled the baton out of Danny's behind and tossed aside, immediately positioning her cock against his gaping hole. She was a bit thicker than the baton but it didn't take much to shove her tip into his asshole.

Danny moaned as his ass was already pretty lubed up and his rectum swallowed Tanya's dong almost instantly. Danny grunted and bit his lower lip as his rectum expanded to accommodate Tanya's member inside of him.

"That's perfect Tanya, punish that slut" Hari said getting up close and personal shots of the two ass fucking.

"Oh-oh-oh-oh fuck-oh" Danny moaned.

Tanya continued pounding away at Danny's ass just like they had done many times by this point. Tanya was getting extra horny. She was thinking about her conversation with Lana and how much she couldn't wait to surprise Danny by submitting to him that weekend.

She grunted and shoved her dick deep inside his asshole getting closer and closer with each passing thrust. She adored seeing Danny dressed in drag and being humiliated in front of all those people. She was so close now.

"Gonna nut" She gritted her teeth.

"Facial! Facial!" Hari reminded her.

Tanya quickly slid out of Danny's ass with a very audible pop and Danny turned around while Tanya forced him onto his knees. He opened his mouth just in time for Tanya to shoot her load all over his face, chin, mouth, and some on the wig while Hari caught it all. It was the perfect money shot.

"There it is! Perfect!"

"Okay slut" Tanya then grabbed Danny and threw the smaller boy over her shoulder. "I'm gonna take you back to the station for more intensive interrogation" she said while Hari got a few more shots.

After the shoot, the two were getting cleaned up inside the trailer. Lana had crept in while Danny was getting his makeup washed off. He and Tanya were both naked and joined by a clothed Hari.

"Excellent shoot you two, this is going great I can tell" Hari reported.

"So, what are we doing tomorrow?" Danny asked eagerly.

"I was thinking slutty cheerleader and shemale coach, maybe you could take a hot load inside you tomorrow" Hari winked. "I think a nice big creampie in your tushy would be the best way to end a great week of shooting" Hari had gotten out the keys to Danny's cock cage lock but she hesitated. There was something so cute and innocent about watching his tiny dick in chastity. She scratched her chin for a moment. "You know, I do want your dick out tomorrow but now I'm thinking, it'd be great if you were locked in chastity all night to maybe get you nice and warmed up for tomorrow...and entice the both of you to keep it in your pants until then" she said. Danny liked the sound of that.

Lana smirked after hearing that, ready to add her two cents. Especially considering she wanted to get a win over on Tanya after their tense conversations and she knew exactly how to do just that.

"Actually, they should both be in chastity" she sugg—ordered.

"What?" Tanya raised an eyebrow.

"Ooh, I like that, you'll be so hard tomorrow you're dick will shoot cum like a cannon, that's not a bad idea, Lana."

"I like it too" Danny beamed, winking at Tanya.

Tanya sort of wanted to object, but any possible plans of Danny fucking her that evening were clearly out of the question anyway, so she sighed and shrugged, spreading her legs out a little bit as her dick was down to normal size again.

"I'll do it" from a drawer Lana took out a much larger cock cage, one big enough to accommodate Tanya's behemoth. She locked her dick in the metal cage and condescendingly twirled the keys afterward, smirking and winking at the Ebony tranny who was less than amused at the whole ordeal.

Her and Danny got a look at themselves in the mirror both with their dicks locked up. They smiled though, as it was a hot ordeal they got to experience together. They had gotten dressed and made the short journey back to Tanya's loft.

They were so horny they barely made it inside before they started to furiously make out. Their evening then consisted of them sharing Tanya's shower dildo and fucking one another on a double sided dildo Tanya had lying around.

She would occasionally smother the boy with her massive ass then reciprocating by bending Danny over the bed on all fours and giving his well spent hole a nice and well deserved rimjob. They continued with mutual spankings with a riding crop with ball gags in their mouths.

Tanya then got out her camera with tripod and the two took turns taking humiliating full frontal shots of the other with their dick in the cock cage before transitioning to some equally sexy and just as humiliating full moon shots. Each would be bound by handcuffs and leg shackles with a ball gag while the other would snap photos. With Tanya's marker they each wrote on the other's ass, for Danny: CUM SLUT #1, and Tanya, the obvious: CUM SLUT #2.

After some more sexy humiliation, the two took a nice shower, washing off all the marker and drifted off to sleep, as the next day would prove to be just as if not more sexual than what they already experienced...yet also set them on a new journey.

They couldn't wait to get to the studio to get their cock privileges back. Tanya was getting her hair and makeup separately while Danny met with Hari, who already had the cock cage keys at the ready.

"You ready to be a slutty cheerleader? I'm super excited for this shoot."

"Absolutely, in fact, I came prepared" Danny winked. He turned around and shamelessly dropped his pants in front of Hari and spread his cheeks, revealing a butt plug inside of him already. Hari was very impressed.

"Oh perfect. That'll get you nice and stretched out for Tanya. Here, let me undo your cage."

Hari stood directly behind Danny, with her crotch rubbing against his exposed rear. Danny blushed as he felt something back there. Hari quickly undid his cage and his cock flopped free, instantly becoming half hard from the current stimulation and the missed opportunities of the previous evening. "You are so fuckable, Danny" Hari cooed.

Danny took off the rest of his clothes and sat in a nearby chair. Hari presented him with what he would be wearing. It was a short midriff in blue and white with an extremely short matching skirt, along with long white tube socks with two blue stripes towards the top and a long wavy blonde wig in a blowout. COCK SLUT SQUAD was emblazoned on the chest.

"Now doesn't this scream: "cum in my ass"? Because I think this perfectly personifies your sissy nature, wouldn't you agree?" she asked.

"Definitely" Danny nodded.

"Great. Okay" Hari motioned for a woman to walk over to Danny with a giant makeup kit. An African-American woman a few years older with dark wavy hair and a fairly tight body was Claudia, another familiar face to the agency. "Danny this is one of our regular makeup girls, Claudia. Claudia, this is our little bottom boy Danny."

"It's nice to meet you Danny" she said then turning to Hari. "Any special requests with this one?"

"Nope, just make him look slutty as you can."

"Not a problem."

"Great"

Hari then left them to go over the days shoot with Tanya but on her way she was stopped by Lana holding up an iPad, and a nearby Tanya definitely took notice, desperately trying to listen in.

"I have proposition" Lana said

"Oh? And what would that be?"

"These two sluts need to be pornstars" Lana glibly explained.

"It is something I've considered in the future, but—"

"But nothing. See for yourself" Lana held up the iPad revealing it was open to a porn website and a shocked Hari noticed the thumbnail was Danny and Tanya from the previous days shoot.

"How did you-..." Hari trailed.

"It was nothing, darling. I do you favor. This merely raw footage, no edits, no acting, no nothing."

"I told you not to interfere" Hari reminded her.

"But Harriet, you want to make money? Fuck magazine. These two, porn gold."

"Lana, I am warning you—"

"Do not take my word for it, see for yourself. Look" Lana showed the view count to Hari, who got wide eyed. "Da, and rising."

"That's a lot of peop—it's been barely one day."

"Like I said, they need to be pornstars. People would line up to watch beefy shemale fuck brains out of sissy teen boy."

"Lana...oh my God, you didn't tell them, that's not legal."

"I tell Tanya I film beforehand. Besides, you think they mind? You think sissy boy minds?" Lana asked.

"That's not the point. You can't just film someone and distribute it without consent, you'd have to blur their faces."

"I edit in post then re-upload, it won't matter, it'll still get rave reviews, not to mention views which makes our pockets heavier, da?"

"You need to understand, there are lines, and once they are drawn you cannot simply cross them. How long before Tanya decides to stop being polite, because I'm telling her this and I'm willing to bet she's not going to be so cordial with you" Hari warned.

"I have ace in hole. You see, she has sissy slut boy whom she likes, and sissy slut boy likes humiliation. She thinks she controls him, but her emotions are for him, and she is controlled by emotion. In roundabout fashion he in fact, controls her. And I believe I can control him" Lana explained wickedly.

"No, you're not gonna fuck Danny into submission."

"Who said fucking? I simply talk, that's all" Lana said assuredly. "You wanted to include film, here is test shot, and is success."

"Okay, assuming I'm okay this, what exactly did you have in mind?" Hari asked pretending to be frustrated.

"Three words: "Sissy Slut School", two students in detention, we sissify bottom bitch boy on camera and hot teacher tops both of them."

Hari sighed, it was a pretty good idea, and one that she was cultivating in her head. She knew how Lana was and how she was clearly trying to take over her project but this opportunity did seem so good.

Simultaneously she promised Tanya she would help stave Danny clear from Lana where it was obvious she wanted to destroy his ass with her cock. She tried to play for both camps with this response.

"No promises, but I will think about it" Hari assured her before walking away, leaving a smirking Lana in her wake.

Back with Danny and Claudia, the latter was touching up some makeup on the witting former. "I hear your really good at getting pounded in the ass" Claudia smirked.

"Oh totally" Danny nodded. "Wait'll you see Tanya, she's massive."

"I can't wait to see her cream you up. I love watching women like her breed sissies."

"Then you're in for quite a show" Danny smiled.

And now over to Hari who stepped over to Tanya's chair, she had just gotten her cock cage removed and was getting some hair and makeup done courtesy of another regular, a blonde bitch with no filter or shame: Ramona. Tanya could obviously see the conversation with Hari and Lana.

"What did the wicked bitch want?" Tanya asked.

"Well, you know she was at your shoot yesterday?"

"How could I forget, that's why I wore that cage on my dick" Tanya groaned.

"Just a formal disclaimer, she filmed it...and then put it online."

Tanya's blood boiled a little bit. It wasn't even that Lana had actually done it, she knew she was filming it anyway, that was something ironically she didn't care much about, it was the fact that she had just done so as if she could knowing she had this air of untouchability about her.

"She told me she was going to film it, but not put it online. Are you shitting me?"

"No, and I am aware she definitely crossed a line."

"Yeah, no fucking shit. I don't even care about the legal BS I'm just sick of her flaunting her influence."

"I agree, but—and she may be bullshitting, I don't think she's interested in Danny."

Tanya raised an eyebrow, she was admittedly taken aback. "Really? He's totally her type."

"Well, she's not interested in that way. I think she wants to manipulate him in other ways. She's very persuasive. If you're not comfortable, you guys can go."

"Nah, we're in too deep already. I just don't want her to force him to be one of your whores, that's all."

"I don't think she wants that. Like I said, he can't drink, all our clients like to go to clubs with our escorts he's not getting in anywhere for three years. I think she genuinely wants you both to do porn" Hari explained.

"Yeah but you know how that will go, Hari" Tanya began. "It'll start out all measured and sophisticated with our "best interests at heart", then it molds into more manipulation and suddenly we start doing things outside the job description, then those things become more commonplace and then it ends up with us sucking strange cocks through bathroom gloryholes in some dive bar in Echo Park while it's being recorded on a nanny cam" Tanya sighed. "Look, it would be hot to be filmed, and I know he's interested and I won't hear the end of it if I just say no. We'll do one test video after this, and if it's good we'll do more."

Hari brimmed at the thought of that, knowing they would come back for more. "Great" then she tried to posit Lana's idea as her own, just in case Tanya had reservations about it. "You know, it'd be pretty hot if you both bottomed together."

Tanya blushed at that thought. "Yeah, it would actually."

"Did you have anyone in mind you'd like to work with? We still have most of our usual suspects working for us that you're familiar with" Hari explained.

Tanya gave it a little thought. "What's Carol Larzaretta doing these days?"

"Carol? Oh she's still around, she does our set designs when she's not acting. It would actually work out cause she is thirsty. Just had a pretty bad breakup."

"Oh no" Tanya sighed with sincerity.

"Yeah, it was like a two year relationship, too. But, that's the past. We can iron out the details later cause he have stuff to shoot!"

Tanya got dressed. Her outfit was a white tight polo V-neck shoving off her huge cleavage with blue and white booty shorts so tight her cock, now already hard made an obvious imprint. She also wore tube socks like Danny, who was now fully dressed in the cheerleader outfit. But he now had pompoms in his hands, one in blue and one in white. Hari walked over to them both and Tanya could see Lana in the background with her camcorder at the ready, she knew this would find its way online and once again, her perverted side wasn't minded, but her practical side was very annoyed about Lana's fast-and-loose power trips.

"Okay you two, you look so hot by the way" Hari began. "I was thinking also Danny really needs a sissy name for this one."

"Any ideas?" Danny asked.

"I like Brittney" Tanya said randomly. "First one that came to mind."

"Brittney works" Danny blushed.

"Perfect" Hari agreed. "Alright, we'll get the regular shots out of the way first, then I was thinking we could lift up some skirt and see—surprise, this cutie's a trap, then maybe a little butt action, then Brittney you can lick and kiss coach Tanya's breasts. Then a quick blowjob, then Tanya maybe you could take out that plug and lick Danny—sorry, Brittney's asshole and then I got something really ambitious" Hari continued. "Tanya I know your famous move, you know the one?"

"The lift and fuck? Yeah, Danny's very familiar" she cooed, rubbing the top of Danny's wig.

"Yeah good, I wanna do that but also if you could, maybe an standing 69? Like you're holding Brittney upside down, you're sucking his ass and he's just choking on your dick, then spin him around and just impale him. Then we can do some more positions until the last is just you bending him over and breeding the shit out of his tushy. Then we can get some good shots of Brittney's hole and call it a day, how does that sound?" Hari asked.

"Yeah."

"sounds great."

"Okay, let's get to first positions everyone." Everyone got ready and Hari started snapping away. "Alright, Danny, do some cheers, maybe jump around just a little bit."

Danny nodded and started to do some moves with the pompoms but obviously wasn't particularly good. He focused on doing a lot of ass shaking. Tanya glanced over at Lana who was filming them obviously, and gave Tanya a condescending wave, knowing she was watching her. Tanya really decided she had to sell this, particularly in making Lana knew whom Danny belonged to. She got into character.

"Look at you doing extra work. You know I've seen you at practice and uh, I was thinking maybe you could do a little more."

"Really?" Danny asked using a super girly voice.

Tanya then pulled Danny's skirt, revealing a super hard cock. "I know you're not like the other cheerleaders, Brittney."

Danny then turned around and bent over so his ass was showing, revealing the plug snugly inside. "Yeah, but I take it in the ass like the other cheerleaders" he cooed.

"I can see that. I think I have a special cheer for you to try" Tanya suggested. She loosened up her v-neck and let her tits pop out.

"Ooh" Danny blushed. "Is this part of it?"

"Absolutely. Now get that face in there." Danny obliged and shoved his mouth into Tanya's left tit while playing with her right breast with her hand.

Tanya could feel Danny's cock rubbing against her crotch and more importantly her dick trapped inside the tight spandex material. She looked down at her sissy boyfriend licking her tits and she was quite satisfied.

Danny quickly moved onto her other boob giving it the same treatment while Tanya moved her hands down to Danny's hips and squeezed his ass while all this of course was captured on camera.

The sissy savored his trans girlfriend's large bosom letting his face disappear into the middle while he motorboated her, to Tanya's delight. She cooed and then glanced over at Lana and was reminded that this was being filmed. Tanya hated Lana for this but she knew it was hot. She felt powerless.

"Alright, good, now let's get to cock sucking" Hari ordered.

Danny released and Tanya did a sexy strip-tease. "Get on your knees, Brittney" Tanya ordered.

He obeyed taking a position he was quite used to by now.

Danny eyed up Tanya's bulge and once the shorts were down, her dick almost hit him in the face. Danny gave her a look as if he was seeing her cock for the first time before sucking up the tip with his lips and going right in.

He made quick motions with his hands on her shaft now being pretty experienced at giving blowjobs to his large dick GF. He looked up at her with wide eyes while Tanya moaned and smiled looking down at him. Hari got behind her and aimed the camera down so getting her dick and the sissy "Brittney" sucking on it.

"Perfect, real nice" Hari said getting back to the other photographers.

"Ooh baby, you're a good little cheerleader, aren't you?" Tanya asked. Danny nodded, releasing from her cock to give her a smile and some hand pumps before going right back in. "Yeah, suck that big dick."

Tanya cooed and used her hands to play with her now exposed breasts. Her gaze again went over to Lana capturing their moment on her amateur camcorder. Tanya took a moment to wonder how many lives were ruined by the content from that thing before remembering it was still hot as fuck.

She more than anything wanted to prove to Lana who owned Danny. Knowing Lana was watching she aggressively grabbed Danny by the back of his head and shoved his face onto her cock and Danny choked it down

"That's really good, Tanya!" Hari called.

Tanya continued to aggressively face-fuck Danny, listening to him choke her member down. A long trail of saliva was escaping his lips and falling onto the floor below. Tanya took her dick out of Danny's mouth letting him take a breath.

"Suck on my balls" she huffed.

She moved her dick out of the way and Danny got his mouth under her proportionately large ball sack and his lips swallowed it. Danny swirled her sack in his mouth while Tanya rested her spit covered cock on top of his wigged head. She played with her breasts again and looked back at Lana.

"Alright, let's move on" Tanya called. Danny let go of her ball sack, now equally as wet as her cock. "Let's go to the 69, I'm feeling ready."

"Uh, okay" Hari shrugged.

Tanya wanted to skip the rimjob, not that she didn't like it, she never minded servicing Danny's butt in any way she could but that particular position made her look submissive and that was not the look she wanted to convey right then.

She quickly grabbed Danny and used some pretty amazing acrobat skills to twist him around while Dany was a bit stunned, he thought this would have happened while he was on the ground and Tanya simply picked him up.

It was a bit touch and go as Tanya was afraid she would drop him but she got a good grip on his mid-section while Danny latched his hands onto her hips. Tanya let the plug stay in his ass while she moved his rear towards her face and started to lick around the plug's base and his taint which made Danny chuckle.

He was pretty impressed how the wig remained on but nevertheless moved his mouth to Tanya's dick and got back to work in this new position but used the same old skills in sucking her off. Hari enjoyed every shot of that.

"Good job, really sell that blowjob Brittney!" Hari called.

Danny did the best he could as all the blood was starting to go to his head but he forced down Tanya's cock into his throat. He enjoyed this kind of humiliation and was really looking forward to being creampied for everyone to see.

Tanya continued to lather up his hole, plug still inside. She wanted to really give it to Danny for no other reason than to prove to Lana she couldn't have him. She could feel his mouth on her dick and could feel some pre-cum drip, she didn't want to cum, not yet. She released and gently put Danny down.

"Alright, let's fuck this bitch!" Tanya huffed, getting tired from keeping him up in an awkward position.

"Okay, let's start to stretch Danny's hole for you, can I get a vibrator on set please?" Hari asked a PA.

"No need, he can take it" Tanya insisted. "He knows he can."

She reached behind him and pulled the plug out of his asshole which instantly puckered. She then picked Danny up, facing her while Danny moved her dick to position. The two looked into the other's eyes and Tanya slowly impaled Danny's ass onto her huge dick.

She could see him blush and moan like a little whore while the two moved up and down slowly in and out trying to get past his sphincter. Danny moaned when Tanya used some tough love and jerked her hips and her dick slid up his rectum while Danny let out a loud feminine moan.

"Aw fuuuuuuuck me!"

Tanya's massive dick ravaged Danny's tight rectum, stretching out his insides with her saliva lubed cock. Her massive member made Danny moan loudly from being impaled on it. The two locked eyes and Tanya started to make out with him.

"Oh that's perfect! I wasn't expecting that" Hari called.

Tanya gripped her hands on Danny's tush, continuing to jerk her hips and letting his ass fall deeper and deeper onto her cock. Danny's dick was visibly under the skirt and he used a free hand to jerk it while the other wrapped around Tanya's shoulders.

"Oh yeah, oh fuck, oh fuck me!"

"You dirty slut!" Tanya chirped.

Danny gripped his legs around Tanya's hips while trying to adjust himself as his rear was becoming accustomed to being pounded hard. He moaned like a little girl as Tanya continued to impale him.

But Tanya was getting very close. She figured she wouldn't have it in her for other positions. This would be now or never lest she blow her load prematurely while trying to switch positions, and that was no good for her.

She took another glance over at Lana and gave her a very convincing stink eye while she filmed the two of them, Lana moaned, her dick rock hard and ready to fire. She wanted to prove exactly who Danny belonged to.

"You're mine, you understand" Tanya whispered. Danny nodded. "You're my sissy slut, don't forget that" Again, Danny nodded.

Tanya bit her lower lip and gave one last moan, thrusting Danny as deep as he could go on her dick before it throbbed and exploded while Tanya let out an orgasmic roar! A roar that was exasperated, sexed up, and tired from lifting Danny up.

"Aw fuuuuuuuck!"

"Ahhhhhhh!" Danny moaned.

Simultaneously, Danny's cock was ready to go from the prostate stimulation and he shot his premature load onto Tanya's bosom just as Tanya shot wave after wave of hot creamy tranny jizz into Danny's rectum, coating his insides with her seed.

"Oh-oh shit! Did she cum? Aw, they both did. Quick, get a close-up" Hari and the other photographers got in while Tanya continued to empty her balls into Danny's tush.

Some cum was leaking out of the sides of Danny's sphincter. Tanya let out her last shot and picked Danny off her cock, while she dripped a few final drops and was coated in its own juices and Danny's saliva.

An ocean of cum fell from Danny like large loogies and onto the floor. Tanya put him down and bent him over one of the white boxes while Danny spread his cheeks and Tanya's cum continued to leak out of his butt pussy.

"I think I was bit premature" Tanya said sort of embarrassed.

"No-no, that was perfect, I loved it. Absolutely loved it" Hari insisted.

Later the two were cleaning themselves up. There was a shower area towards the back of the studio, acting like a quasi-locker room. A naked Danny as about to shower and was joined by Tanya.

"That was so hot, babe" Danny winked.

"I know" Tanya cooed. She looked around, remembering a bag she brought with her. "Hey, where'd I leave my shampoo?" she asked.

"Oh shit, it's in the bag back in the studio. I can get it."

"No-no baby you shower I'll be right back."

Tanya then paused. She really wanted Danny to fuck her. Tiny dick or not, it was still a dick and she was still a woman with needs and she wanted to desperately prove Lana wrong. To be honest she couldn't have thought of a better opportunity to act on it.

"And when I do, I have a special proposition for you" she winked and wrapped a towel around her, walking out into the studio.

Unfortunately, that was the opportunity a certain someone was hoping for. While Danny continued to shower, he didn't notice Lana enter the shower room and he was startled to see her standing outside.

"What the?"

"I didn't mean to startle you. We not been formally introduced. I am Svetlana, I own this studio with Harriet."

Danny gulped, he had been in the same room with her but the two were never introduced, he tried to be polite knowing he didn't want to cross Lana as per Tanya's multiple warnings not to do so.

"I'm D-Danny Lowry."

"You are very sexy sissy boy, Danny" Lana cooed, taking one step closer. Danny recoiled, and she took a step back. "Harriet tells me you like photography?"

"Um, yeah. Graphic art, stuff like that."

"Well you are in right place. I need photographers in my studio, ones who do not care to capture skin on camera. You seem to be so inclined."

"Uh, erm, yeah" Danny said nervously. He looked down at Lana's pantsuit and saw a bulge in her pants.

"Tell me, what would you do for such an honor, hmm?" Lana asked. "I see you make good anal bitch."

"Well um, I've taken a few cocks up my ass, sure" Danny nodded.

"How would you and Tanya like to take many tranny cocks up your asses? I was thinking you both would be perfect bottom sissy pornstars."

"But, what does that have to do with the photography angle?" Danny asked.

"You start at bottom, you work your way up. You two give me a few months as pornstars for my firm—for movies Harriet directs and I make you both photographers, highest pay in industry, health benefits, whatever you'd like."

Danny did some quick thinking, that did sound enticing. But he knew he should talk this over with Tanya. Then again, he didn't know how long this offer would last. Plus, he was really enjoying being a little cock slut for the camera, and a few months didn't seem like that long to him.

He unfortunately was thinking with his dick, now starting to get hard once more from the very thought of it all. He knew this would be a losing battle as Lana could see his rising member with the shower water hitting it.

"You seem interested?" Lana said pointing to his dick.

"Um-uh, well. I-I-I-I need to-t-to t-t-talk to Tanya a-bout it" he stammered.

"She do so much thinking for you. I know you sissy slut but you still man. Take charge, you make decision. You must act now, Danny. If I leave room, offer is off table" Lana warned.

Danny stammered yet again. He couldn't say anything. He didn't want to merely make the decision for the two of them and Lana wasn't making the process any easier as he could see she was slowly backing up towards the door.

Tanya had been making all the decisions for them and he felt like this couldn't be so hard, after all it wasn't like the two weren't interested in being fucked for the camera. His dick clearly making the decision for him, especially knowing the reward would be pretty sweet, Danny called.

"Wait!" Lana smirked and then faced him. "We'll do it."

"Excellent. Now..." Lana reached into her pocket and held another pink cock cage. "I need you to wear this, so your dick nice and ready for shoot. Is professional courtesy" Lana lied.

"Really? People wear those before shoots?" Danny asked.

"Oh da, so their dicks hard and ready, you not noticed today?" she asked

Danny did have to admit, being in chastity did help with his orgasm, and it was pretty hot. "Um, sure, I g-guess."

"Good, cause is non-negotiable. Come here."

Lana knelt down in front of the shower and grabbed Danny's ball sack to help bring his cock down and then forced his now flaccid member into the cage and locked it up. "You made wise choice, Danny. I look forward to working with you both" Lana winked while Danny made a nervous nod.

She left the room just as Tanya, now with her bag, was about to walk in. She got wide eyed after seeing the smiling Lana leave with supposedly only her and her man alone, which is what she truly feared.

"What did you do?"

"Nothing, I did nothing" Lana smirked, then walked away.

Tanya rushed into the bathroom and saw Danny with the cage on his cock and now tears streaming down his face as he realized what he had just done. "Tanya I-I can, I can explain!"

Slightly mad, Tanya knew how manipulative Lana was. And she wanted to prove her wrong. Her and Lana were not one in the same. She ran over and simply gave him a hug. "It's okay baby. It's okay."

She got dressed and marched towards Lana's office, slamming the door behind her. Lana was on a phone call which Tanya immediately interrupted by pressing the end button on the receiver.

"Hey! That was important call—"

"What did I tell you!? I told you multiple times and you fucking ignored me!?" Tanya boomed.

"I did not fuck sissy Danny, I merely made him offer he couldn't refuse...or for you either."

"What are you talking about?"

"You want to get back in photography? Give me three months as sissy pornstars and I make that reality, he chose for both you" Lana explained.

"Right, I'm sure you didn't give him much of a choice."

"He thought with his tiny cock. It was right move" Lana chuckled. "You come here, to my studio and you tell me what to do. Did you not think—in years of knowing me I was going to take that? Or was I going to try something sneaky and deceptive? This your fault."

"Do not deflect your egregious behavior on me!" Tanya sneered. "I know how you are with the young men that work here, I was trying to protect him."

"You knew best option was to stay away but you thought you could work with Harriet and I would just sit around with dick in hand? If you truly cared you would have told her no and ended it there, instead you come to me, you harass me and I respond. I did not force Danny to have sex with me...yet, and I make dreams come true."

"I'm not working with you, and you're right, fine. We're done, and you can tell Hari why we left. Now give me the fucking keys."

"What keys?" Lana coyly asked.

"Don't play dumb, the keys to the cage."

"Oh right, I no have them."

Tanya was taken aback. "What?"

"But I can get my hands on them say...day after next, when we shoot first movie" Lana smiled.

Tanya grunted. "I don't believe you."

"Yes you do, but you and sissy Danny had judgment clouded with sexual humiliation, which is clearly how he likes it. And you knew what we do here. You know me, Tanya. How did you not see this coming? You know you are not me, but my chiding made you headstrong, you make mistakes, and I capitalized."

Tanya grunted, she wanted to slam the desk over Lana's head, but yet, she didn't. She could have shaken Lana down for the keys but figured this fight would get ugly. She again proved Lana's point, going from her reserved tough self and once again thinking with her dick...or maybe Lana was just always in four dimensional chess mode? She acquiesced.

"Three months?"

"Three months" Lana retorted. "Top pay, benefits, you leave with photography job."

Tanya then had a slight smile creep onto her face. "You do realize I will get back at you for this."

"And I will be prepared. Now, before you go, I need to give you this" From under her desk, Lana took out another large cock cage. Tanya did the math and shook her head.

"Uh-uh. No way!"

"Then I rescind offer, and you know, my memory...where did those keys go?" Lana taunted Tanya.

Tanya grumbled. She didn't want to be in chastity, but she knew Danny liked it and it was pretty hot for what it was worth. She felt like she had no choice short of getting violent and she didn't want it to go to that...despite there being many other options for her to pursue. Once again, she let her horniness get the better of her.

She dropped her pants and let her dick flop free. Lana quickly put it in the cage and Tanya pulled her pants up. "Happy?"

"Thrilled. Day after next we film first movie: sissy slut school" she smirked. "I knew I could get to you through him, I just needed right angle you see." Tanya rolled her eyes and sighed, not wanting to say something she would regret, she went to the door. Lana stopped her. "Tanya?" Tanya then stopped, not looking at Lana. "And that is how I win" she smirked. Tanya groaned and left, slamming the door behind them. Tanya passed Hari in the hall but didn't say anything.

Hari then entered, knowing something definitely happened. "What was that?" she asked.

"We start filming day after next. Who would you like to use?" Lana asked.

"Um, I was thinking Carol Larzaretta."

"Ooh, beautiful. I like it" Lana smiled.

Later, Tanya and Danny were now dressed and climbed into Tanya's car. The two looked at one another. "Now what?" Danny asked.

"Now, we can plot...but in the meantime, we do have some hot times ahead, don't we?"

"Yeah. I-I'm so sorry Ta—"

Tanya stopped him by plowing her lips into his, then quickly released. "Don't be. I dragged you into this, more or less. We'll get back at her, and then get back on track."

The two smiled and Tanya drove away to her loft with many sexy times ahead of them...

**Notes for the Chapter:**

> Think of any scenes or situations you want Danny and Tanya to be in. Make a comment with those suggestions and thanks for reading.

**Author's Note:**

> Kindly leave me comments with your suggestions and they might show up in future chapters. Also, at some point Tanya is going to have Danny get a tattoo on his ass to brand him hers. What should that tattoo say? Leave a comment with your suggestions.


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